editione1.0.1
Updated August 22, 2022You’re reading an excerpt of Founding Sales: The Early-Stage Go-To-Market Handbook, a book by Pete Kazanjy. The most in-depth, tactical handbook ever written for early-stage B2B sales, it distills early sales first principles and teaches the skills required, from being a founder selling to being an early salesperson and a sales leader. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, commentary and future updates, and a high-quality PDF download.
Now that you’ve gone and invested all this time and energy in hiring sales staff, the next step is to get the most out of your investment. You want to get new hires up to speed—selling and closing business—in the shortest amount of time possible.
In early-stage B2B sales, once you’ve hit product/market fit, your biggest cost is the opportunity cost from missed, or even just delayed, sales. This is especially true in greenfield markets, where the competitive landscape is only just forming and it’s a true landgrab. The salesperson you haven’t hired yet, and haven’t gotten productive yet, isn’t generating the ~$50K, ~$100K, ~$200K a month in sales they could be. Consider the future value of those customers as they recur, proliferate, and refer other customers, and that lost revenue looks even more troubling.
Moreover, if you are losing 30–50% of each sales hiring class to flameouts, in part due to faulty onboarding, you are eating this terrible opportunity cost again and again—not to mention the pure cost of the time, treasure, and energy put into recruiting those flamed-out reps.
This is why the lack of rigor around sales onboarding in so many organizations astounds me. You’ve ideally done an excellent job (and presumably spent a lot of time) screening and interviewing your new hires. Why would you then half-ass their liftoff? Why spend the time and money to get a great race car, but not tune it up, fill it with premium, and top off the tires? Why risk a failure to launch?
Yes, there is a temptation to get new hires facing customers as quickly as possible. See previous comment about opportunity cost of lost and delayed sales. This is a false economy. You will simply be burning good leads and injuring new reps’ confidence and, ultimately, their chance for success. Mitch and Murray paid good money for those Glengarry leads, and they would be wasted on your poorly onboarded staff.
If you are hiring experienced staff, there is also a temptation to rely on their ostensible expertise and let them do their thing. But you are making false assumptions, and it will bite you. You have no idea what bad habits their past organizations have instilled in them, or what gaps there are in their knowledge of the market.
Resist the temptation to shortcut onboarding. In an evangelical, consultative sale—the kind your staff is most likely engaged in—business and product expertise is vital. Equally important are high-impact presentation and demonstration skills, persuasive objection handling, and the basic blocking and tackling of CRM, calendar, and email excellence. Relying on your staff to simply know this is a losing proposition.
Instead, design the right sales boot camp for your team—a week to two weeks of rigorous onboarding—and implement it with your newly hired classes. Every time. Depending on the complexity of your offerings, you might find that you need even longer. This boot camp should include pre-onboarding homework and acclimation to your company culture, lessons in business and market subject matter and product, tooling and process training, drilling and repetitions, and eventually ramp and monitoring.
Hire right. Enable right. Position your human capital for success. You won’t be sorry.
So what should your boot camp look like? I prefer a university-style onboarding for new hires, with a singular focus on imparting the knowledge required for high-impact selling conversations. You will be hiring smart; now the goal is to fill those brains with the necessary information, and then run them through enough repetitions that muscle memory takes hold and your hires’ confidence grows.
Remember, like a university, you want to be conducting this training with cohorts and classes. The traditional thinking in sales management is that you’ll lose 30–50% of each class within six months of hiring them. That statistic is frightening; I believe that with proper screening and onboarding, you can have a much higher yield. However, even if you’re amazing at hiring, it’s a similar amount of work to onboard four salespeople as it is to onboard one. They’re all sitting there, listening to the same instructor (you), so why not force multiply? You can even give them team names and use training cohorts as a chance to foster a sense of shared identity. TalentBin classes included Gryffindor and The Three Amigos, underscoring a notion of shared identity. Onboarding a class creates a sense of both competition and camaraderie that pays off: one person may miss something, but his teammate didn’t, and they can help each other out. And when it comes time for sales drills, you have natural sparring partners. Hire in classes and run your onboarding as classes too.
As for your curriculum, obviously as your go-to-market strategy evolves—and you learn as you go—you’ll fine-tune it. When you start out, it could simply be a really big Google Doc that you fork with each new class, highlighting sections in green as you cover them. That may eventually turn into a series of Google Docs, each linked to a Google Spreadsheet checklist to track the execution of each class. We started this way, and after a couple iterations our sales ops lead, Manny Ortega, codified a pretty curriculum in Google Docs. From there, you can go all the way up to onboarding software, like Parklet or Kin, that tracks (in a much fancier way than a spreadsheet) the execution of each step. The important thing is to have a holistic set of topics to cover, and to work your way—exhaustively—through them each time, adding and removing as you go.
These are the general buckets that I have included in each iteration of my onboarding curriculum.
You can start onboarding before your hiring class’s first day on the job. Whether you’re hiring new grads who are taking a break before starting their first job as a market development rep (I’m partial to this) or pulling new sales reps into the organization from a similar role at a different company, new hires will often have a certain amount of excitement and momentum headed toward your organization. Capitalize on that by assigning a not-insignificant amount of work ahead of time, to better prepare them to hit the ground running when they arrive.
Pre-work has the added benefit of ensuring that new hires are tracking correctly and won’t fall victim to cold feet, or counter offers from their existing employers. They’re not truly hired till their butts are in seats on your sales floor, so engaging them even before they arrive helps.
What manner of pre-work should you assign? It depends on what materials you have available, but a mixture of readings, presentations, and recordings is good. Because we record our demos at TalentBin, we have a library of awesome calls and terrible calls, organized by customer type (enterprise vs. mid-market vs. SMB, and staffing agencies of varying sizes); I ask new hires to watch a set of those ahead of time. You might include any recorded feature demo videos or webinars; if you have a support portal with video content, that could work too. Just provide new hires a set of hyperlinks to work through (and don’t rely on the abstract, “Go review these materials”).
If there are particular readings that are appropriate, assign those. There are some books on technical recruiting for nontechnical recruiters out there, which TalentBin has used to put together a course reader of sorts. You could also just assemble an assortment of hyperlinks from relevant blog posts. If there are any whole books that your organization is partial to, assign those. I’m a big fan of The Goal, to get sales staff into a goal-oriented, deductive-reasoning mindset, and Getting Things Done, to stimulate an office-efficiency mindset, and The Score Takes Care of Itself as an introduction to the importance of sales precursor behaviors being connected to outcomes. Just be sure that everything you assign is high quality and relevant; mere busywork sets the wrong tone and feels like a chore. Also be mindful of the total amount of pre-work you assign, relative to how much time your hires have before their first day. Ten hours of work over two weeks is probably a fine amount.
importantLastly, they should know that their execution will be monitored and audited. (Just like CRM! Welcome to sales!) You need to say, “Here’s this. It’s not optional. It’s important. There will be a test.” Deliver the materials in a manner that allows you to openly track progress, and which they know you have the ability to track. This can be as easy as sharing them in a Google Doc and instructing new hires to highlight the sections as they complete them.
Don’t forget, there is pre-work for you too. When your new staffer shows up on day one, their first impression is what will start them on the right, or wrong, foot. Make sure that all of their technical infrastructure (laptop, monitor, mouse, and so forth) is in place and at least cursorily set up. Provide any other materials they’re expected to make use of in their day-to-day. (I’m a fan of lab notebooks—and graph paper, clearly, high-quality pens, Post-it notes, pen cup, and so on) And if you have it (and you should), put out some quality schwag, like a company T-shirt, sweatshirt, travel coffee mug, water bottle, and so forth. A new staffer’s desk should look like the organization was waiting for them with bated breath and executed preparations accordingly. It should say, “We’re glad you’re here. This is how we do things. You will too.”
Of course, there will be all manner of standard forms that you need to take care of, like W-2s, payroll setup, direct deposit, any stock 83(b) forms, and so forth. I recommend setting aside time for side-by-side execution with each new hire to get this out of the way. Unfamiliar forms can be confusing, which is unpleasant for new hires and risks casting a pall over the rest of your onboarding. Crank out the paperwork so you can move on to the important stuff.
Acclimating your new hires to your company’s values isn’t just a single conversation; it’s the way you demonstrate how your organization executes, what is celebrated, and what is censured. This is the case during onboarding, but also day-to-day. However, I find it important to have a proactive, explicit, candid discussion of what is valued within your sales organization and what is not okay.
In the TalentBin sales organization, we lived by three key tenets:
You don’t have to be an engineer to operate with an engineering mindset.
We are the product managers of our sales organization.
Intellectual honesty is paramount.
We explain them to new hires as follows:
exampleBecause the sales team grew out of the engineering and product organization and was built by a non-sales person, and because for much of TalentBin’s early existence, we were leanly capitalized and had to make do with fewer humans, heavily leveraged with technology—we like to say that we have an engineering mindset. Our approach is to identify constraints, propose solutions, test them, and then either reject or embrace the outcome. Rinse, repeat.
Similarly, because there are only so many things we can work on at one time, we have to prioritize resolving identified issues based on their impact on revenue. We refer to features of the sales organization, whether process, tooling, or materials, and hold ourselves responsible for product managing the sales organization in this conceptual frame.
Lastly, TalentBin itself was the child of initial failed product hypotheses and subsequent pivots toward success. The organization is highly aware of both the perils of sticking your head in the sand and the benefits of eyes-wide-open self-assessment, regardless of the outcome. We value intellectual honesty in the sales organization, just as you might in an engineering organization.
Better, of course, to start articulating these tenets in your hiring process. Once you’ve identified your organization’s values, you can look and screen for candidates that exhibit them. By articulating how you roll from the get-go, you can also excite potential hires for whom those tenets are compelling and allow bad fits to disqualify themselves.
Finally, a great way to contextualize the important pieces of your culture is to frame them in your organizational history, as in, “This is where we started, this is where we’ve gone, this is where we are, and this is where we’re going.” A robust review of the organization’s path (both your company’s and the sales team’s specifically) is important in and of itself for cultural onboarding, but can also be a useful way to underscore key themes.
It’s likely that your organization will be selling an innovative solution that, while it fits into an existing market, is a substantial departure from existing products.
Because your sales staff will be engaged in presenting this new, less proven solution in an evangelical and consultative fashion, they will need to be expert in the market, business drivers, and technical realities of your solution. They need to be able to sell authoritatively, interacting with customers as equals, not just vendors.
All of the above speaks to the importance of a rigorous general subject-matter onboarding process.
When you start out, it should be sufficient to simply cover this training with basic materials (slides, and so on). As you scale, though, you may find it valuable to construct a testing harness that ensures reps are retaining material or, if they’re not, requires them to re-review the materials before they test out. Early on, this is likely not necessary. But if you’re trying to onboard 500 sales reps, distributed across geographies, it’s kinda required.
You may have additions, but the subject-matter buckets we focus on at TalentBin are market understanding, business driver understanding, and technical understanding.
There’s very little chance that your solution operates in a vacuum, so it’s important for your staff to understand the market. What is the field in which your solution operates? How has it evolved over time? What are the big epochs of technology that have impacted the market? What is the current state of the market, and who are the major solution vendors that operate in your space—especially those that are tangential to your solution?
If you work in the human capital management market, you would want to cover job boards, recruiting workflow software, and even downstream solutions like HCM cloud suites that include onboarding, learning and development, and performance management stories.
Or if you work in the sales automation/customer relationship management space, it would be important to cover marketing automation and campaign management solutions in front of your solution, other CRM players (past and present), and various add-ons, along with downstream finance and enterprise resource planning solutions.
You don’t want a customer who asks how your solution interfaces with a tangential workflow solution (“How do these candidates get into our applicant tracking system?”) to be met with silence across the phone line.
Our training includes a full hour session on the history and state of the art of the talent acquisition space as impacted by the internet, including job boards, applicant tracking systems, large recruiting agencies, professional social networks, and the large HCM and recruiting workflow players that all work together.
If you are selling to the recruiting market, then it’s important to know all the things that will be important to your client: number of inbound candidates, quality of candidate, response rate of candidates, cost per hire, time to hire, quality of hire, and hiring funnel drop-off (from engagement to phone screen to interview to offer). For staffing agencies, which are focused on earning fees from client placements, metrics around new candidates discovered, outreach per day, submittals per week, and eventually placements will be the key metrics. If your solution can increase the amount of outreach in a given amount of time, increase response rates of candidates, increase submittals, reduce cost of hire, or reduce time to hire, and do so by substantially more than its cost, you’re in business.
If you’re in the sales and marketing automation space, the key metrics might be number of qualified leads per week, cost per lead, calls per day, presentations per rep per week, close rates, bookings per rep per month, and so on.
Whatever space you’re in, the first step to being able to have a consultative conversation with a potential client is to understand the base economics of their business.
The way that we achieved this at TalentBin was by having one of our sales team, Brad Snider—a former technical recruiter—give a rundown on all things recruiting in a live hour-long class. We called it The Brad Class. It was always awesome because Brad knew his stuff cold and was a great storyteller (which makes for a great sales rep too!). The class covered in-house recruiting, agency recruiting, recruitment process outsourcing (RPO) recruiting, and the key parts of the recruiting cycle, plus business drivers for each. Later we recorded it, and we have had hundreds of sales reps and customer success staff watch (and be tested) on it.
However you want to approach training, just make sure that you’re preparing your staff with a base-level understanding of the business drivers they’re working with. Their understanding won’t be perfect, but it will provide groundwork for them to build on as they have more sales conversations.
As a founder or senior executive on your team, you likely have extensive technical understanding of your space. But this will certainly not be the case with all of the reps that you hire. (Ideally you’re hiring for this acumen, though.) Just as you need to ensure that your team understands the market and your clients’ business drivers, you need to familiarize them with the key technological drivers in your space too.
TalentBin is a great technical recruiting solution. However, not every sales rep we hire (and not every recruiter we sell to) will have the technical underpinnings, to start, to understand that Java and JavaScript are not the same thing. If you work in, say, storage, nontechnical staff might not immediately understand the differences between spinning hard drives and flash, storage area networks (SANs) and network attached storage (NAS).
The important thing is not to cover each and every technical component out there, but to focus on the most important terms and innovations. Again, your goal is to provide a base layer of information for reps to build on—the understanding to engage in consultative and authoritative conversations with prospects from the get-go.
exampleThe way we handle this at TalentBin relates specifically to technical recruiting. Ensuring that our staff knows the difference between a front-end technology and a back-end technology, SQL and NoSQL, or scripting and compiled languages makes them much better sales staff. I want my team to have compelling conversations with their technical recruiting prospects—often, they’re more authoritative and grounded than the folks they are selling to.
There’s a reason we’ve made it this far into the chapter before we even started talking about the specifics of your product and how to present it. Your solution exists in the context of a larger market, and it’s critical for reps to understand that before you delve into your particular solution. One builds on the other, and if you start in on your solution before your staff understands the problem space, they’ll be seriously hampered in presenting it in a persuasive, high-impact fashion.
But once that foundation is in place, take the time to give new staff a thorough education in your product and how it should be presented to the market.
Rather than diving right into training on the pure sales presentation and customer-facing demo, I like to start by giving staff a less formal product walk-through. Specifically, we look at all the key elements of the product, correlating them to use cases for our users, all while speaking to the business drivers each feature addresses.
To achieve the above, you can use an abridged version of your customer-facing demo (the structure for which I address in much more detail in Early-Stage Sales Materials Basics.
As with other topics, this product walk-through can simply be presented to new staff, or, in a more scaled onboarding environment, it can be tested on too, with quizzing software.
Once you’ve walked through the product, you’re ready to move on to a more formal sales presentation training. Because of the pre-work that you’ve assigned, which ideally included recordings of your sales presentation and demo, your reps should already be familiar with your approach. The goal of this class is both to do a one-on-one (or, one-on-group, if you have a class of four reps, say) presentation and to contextualize the different chapters or sections of your presentation.
Because your presentation should have chapters, with individual slides supporting the general thrust of each one. Go through these chapters with your new hires, contextualizing the intention of each, and explain how your slides support those goals. This will be important later in your onboarding process, when you start drills and repetitions. (For more detail on sales presentation construction, visit Early-Stage Sales Materials Basics.)
Having completed this more formal sales presentation breakdown, I like to train reps on the various segments of an actual sales demo. This is different from the initial walk-through; it’s a mock demonstration—live, to the class—in the style you would use with a customer.
Like your sales presentation, your demo ought to have sections—dedicated to presenting the various parts of the product that resolve the business pains you’re attacking—and those sections should flow logically. Take this opportunity to contextualize each section for the class, as in “the point of this section is to demonstrate features A, B, and C, which are designed to help the user do X, Y, and Z, which solves business pain M, N, and O.” Do this for each section while the team follows along, asks questions, and takes notes.
Often new sales reps who haven’t made a strong connection between the features they are presenting and the business pains they aim to solve will end up presenting features in a “Now we have this, and now we have this, and over here we have this” fashion, without connecting them to use cases. This makes for a wholly uncompelling demo that relies on the prospect to make that association—which they may, but there’s no reason to risk that. The goal of this class is to set the groundwork for presentation and demo drilling, and to give new reps a framework for presenting features and functionality in the most compelling fashion possible.
One thing that I don’t spend much time on during onboarding is objection handling. You will hear myriad potential objections from your prospects, so trying to go through them all is a losing proposition. Instead, try to fold in common objections or prospect confusion throughout the rest of the sections of onboarding—presentation, demo, and so on. Keeping an exhaustive list of common objections for reference is certainly helpful, and letting reps know where it lives and how to use it is helpful too. But you need not tackle each one at this juncture.
Depending on the amount of competition in your market, dedicating a section of onboarding to reviewing the competitive landscape can be useful. I suggest tackling this after the market landscape, business driver, technology, and product sections, because there will then be a conceptual framework in place for reps to understand key differences between competitors. Ideally you already have competitive product marketing materials in place, so utilize them for this class.
While cultural, market, business driver, and product expertise onboarding lays the foundation for sales rep success, it’s important to not underestimate the importance of training in the nuts and bolts of tools and processes.
The modern sales rep ought to be a software-enabled, highly levered professional. An average day will include office basics like email and calendaring and sales standards like Salesforce.com, all the way to more advanced software like email open and click tracking and presentation software like Showpad. If you simply assume your staff understands how to use the tools you provide, and use them well, you run the risk of setting them up to underperform.
An often-overlooked part of onboarding is simply provisioning the proper tools for success. You might be chuckling to yourself, wondering how that could possibly be overlooked, but you’d be surprised how often it happens.
Before your new hires show up, make sure that you have purchased all the equipment your existing staff is expected to use in their day-to-day—even better if you already have a Google Spreadsheet listing all the pieces of hardware and software that will need to be set up (ideally with a hyperlink to the item on Amazon, for easy ordering in the future).
exampleFor us at TalentBin, this amounts to a desk (sitting or standing), chair (yes, seriously, this basic—I’ve seen new hires show up to find that there’s no chair ready for them) or standing foot pad and task stool, laptop, external monitor, laptop stand, keyboard, mouse (with navigation buttons for rapid browsing), mouse pad, desk phone, and headset, all the way down to lab notebook (graph paper preferred), pen cup, and high-quality pens.
This level of specificity may seem odd, but it all comes down to equipping for expectations. TalentBin sales staff are expected to use their lab notebooks to record discovery question results and other notes from every call for later transfer to Salesforce.com—so providing lab notebooks and high-quality, pleasurable rolling ball pens is the first step. If they don’t do it, there’s no excuse; the very existence of the equipment reinforces the expectation. Same with standing pads, headsets, and so forth. If you have an expectation for high performance, equip for it and train for it. The salary expense of quality sales staff far outstrips the capital cost of a quality headset, pens, and monitors—and the opportunity cost of lost ~$10K deals certainly far outstrips any of these other expenses.
Pre-provision your staff’s software too, so you can get down to actual value-adding onboarding activities faster. We’ll get into configuration in a second; I recommend holding off on that and tackling it in a group setting. But for things that can be stood up ahead of time, do it. It demonstrates to your staff a mindset of preparedness.
exampleAt TalentBin, this meant that every new sales rep was ready to go with a Google Apps identity, a Salesforce account, an Act-On sales account for Salesforce, Yesware for email open and click tracking from Gmail, ClearSlide and InsideSales.com’s Click to Call for account executives, InsideSales.com’s PowerDialer for market development reps, and RingCentral phone accounts. Typically, you can quickly provision these software offerings from a single administrator dashboard. Also, make sure to add new staffers to all relevant recurring meetings—like your sales team meeting, standups, all-hands, one-on-ones, and pipeline meetings.
Lastly, and I mentioned this in Cultural Onboarding, is schwag—shirts, hoodies, water bottles, coffee mugs, pint glasses, pens, Post-its. (And for morale and customer-relations reasons, not marketing reasons, I recommend investing in schwag.) Make sure that these items are present and accounted for on your new hires’ desks on their start dates.
Not only does pre-provisioning make your onboarding more efficient, it sets the tone from the moment your hires show up: you mean business and have a culture of preparation and execution, from hardware to software to T-shirts.
While pre-provisioning equipment and accounts is efficient, I recommend stopping short of meaningful configuration, largely because it’s often more efficient to have four or five people in a conference concurrently setting up, say, their email signatures than for you to do it individually. The act of configuration can also be an important first step in training your staff to get the most out of the tools you provide.
As with your hardware and software provisioning checklist, it’s crucial to codify your configuration steps in a Google Spreadsheet. Simply block off an hour or two, and with your newly onboarding cohort, walk down the list, configuring as relevant and speaking briefly about usage. At TalentBin, these configuration parties include:
Google Chrome setup (and proper bookmarking)
Gmail setup: creating email signatures and turning on keyboard shortcuts, undo send, send and archive, auto-advance, and other enablers of inbox zero
adding browser and Gmail plug-ins, like Rapportive, Yesware (along with BCC to CRM setup) and some of our custom-developed plug-ins for lead generation
voicemail setup for phone
Jing for screenshotting and screencasting
setting up corporate email on iPhone or Android
a demo environment in the product they’ll be selling
You’ll customize your own list as you go. The point is simply that you shouldn’t leave it up to the reps to do it by themselves. It either won’t be done, or it will be done poorly.
After configuration is complete, it’s time for pure tool training. If you have given your staff a tool to use, and expect them to use it, you need to train on it (and the cost of that training should be baked into any purchase decisions). Assuming they know how to use it is a recipe for disaster. But it’s also important to recognize that you’re never going to cover everything, and mastering these tools is a process. You’re just laying the groundwork and setting your reps up for better adoption.
And when I say you need to cover all the tools your staff is expected to use, I mean all—from the most basic to the more advanced.
When you’re hiring staff that may be fresh out of college, office basics—ones that may be standard for someone who’s been in the industry for five years—will actually be quite foreign. Similarly, if you’re hiring more senior staff, you never know what sort of bad habits they may have, or what their prior employers failed to train on.
exampleAt TalentBin, the basics we cover start with the browser. (Yes. This basic.) Our team standardizes on Google Chrome because of its speed and broad plug-in support. We train on the Getting Things Done mindset: closing tabs that are no longer needed (to clear cruft from one’s workspace); creating a new window for a new task that may spawn new tabs (to avoid the case of dozens of confusing tabs, and a confused sales rep); closing windows when a task is complete; and mastering a variety of keyboard shortcuts. In a nutshell, we include anything that will make our reps more efficient and save them from distracting off-ramps from execution.
Basics training extends to Gmail and calendaring as well. Email is extremely powerful, and extremely dangerous when misused. In sales, it’s a great way to create multiple touchpoints with clients in a scaled way, to deliver impactful collateral, and to juggle many concurrent conversations in a way that is documented and CRM-able. It can also be a massive time suck, and without discipline, your reps’ inboxes will become a disaster of erroneous, unimportant emails (“Would you like to attend DreamForce!?!?!?! Click here!”) mixed in with extremely high-value client communications (“Can you send me a contract for 10 seats?”).
The Getting Things Done notion applies to email too. The idea that if there’s not a next action on an email, you should archive it and get it out of your inbox is a new concept for most reps. Teach it (and later, audit it—when I come up to a rep and they have an already-read, not important email still in their inbox, they hear about it) and connect that lesson to the additional functionality in Gmail that you need to have turned on in your configuration party. (This works with Outlook as well: remove all email push notifications that lead to treating email as instant messaging, and train reps to close their email and work out of their CRM and calendar—their actual to-do lists.)
Train on well-written emails. Show reps how to write clear, topical subject lines (no, not, “Quick question” or, “Hi”); how to use cc appropriately and reply-all to ensure thread continuity; and how to compose messages that have sufficient white space for readability, use bold, bullets, and headings to identify key sections of an email, and ensure that individuals being responded to are properly called out. Show how to write for searchability, so you can easily recall a message from your Gmail archive. Show how to proofread, and set expectations around rigor and grammatical excellence in client-facing communication. (Ideally you screened for this in hiring, but it’s good to reiterate.) Make it clear that these factors will be audited in the CRM as all email communications to clients are captured.
Train on a templating mindset. Common, repeated, sales communications take up a disproportionate portion of a rep’s time, so templating can be a massive time saver and can reduce errors (grammatical, and otherwise). Helping reps embrace this (by both example and explicit statement) will make this top of mind. After onboarding, continue to demonstrate this by providing templates for new product releases, but also by encouraging reps to create their own. Create a culture of template sharing—most reps will have the same needs, and a tool created by Rep A will likely apply to Reps B, C, and D. Just make sure templates aren’t stored in email, but in a common repository for recall and access.
Lastly, train on keystroke shortcuts. Gmail’s keystrokes are amazing. You turned them on in your configuration party, now train reps on how to use them: J/K to navigate up and down their inbox, X to rapidly select unimportant emails, and E to archive them are extremely helpful for maintaining a clean inbox. C to compose a new email, Command-Enter to send it, Enter to open a message, R to reply to it, and GI to get to your inbox will help reps be quick and efficient with their communications and drive more outreach and response in a given time period. Print out the Gmail shortcut cheat sheet and provide it to all your reps. All of this will not only keep them from being lost in Inbox Hell (and losing contracts in there) but make them email ninjas.
With sales, all you have is your time. Training on calendar excellence should not be overlooked. This comes down to two things: using your calendar to manage others (prospects) and using your calendar to manage yourself.
Many first-time staff will be unfamiliar with the notion of sending meeting invites, and that the sending, confirmation, and declining of those invites is an important part of enterprise sales. So show them how this is done, and what to include in a compelling calendar invite: venue information, a clear and actionable title, and agenda items in the body (what is to be covered?), along with a repetition of venue specifics (Zoom link, join.me, phone bridge, for example). Setting expectations here will lead your staff to better meetings and fewer cancellations.
Once you’ve covered the basics, move to the sales-specific tool chain. This is where you may end up with more variation in what you need to cover. However, there are some important common denominators.
The basis of any high-performance sales organization will be excellent use of CRM, as it is the central hub for activity, efficiency, and reporting. Every time I help out a sales organization that’s on the rocks, invariably so many of their issues come back to CRM fragility. We use Salesforce, so I’ll largely tailor this conversation around that (but you can easily swap it for your own preferred CRM).
From the start, make it clear that, “If it’s not in Salesforce, it doesn’t count.” If you are basing reporting, activity tracking, and so forth out of Salesforce, it needs to be clear that if a demo happens outside of Salesforce it doesn’t count. Or get paid. If emailing happens that isn’t bcc’d into Salesforce, it doesn’t count. Set this expectation now, and audit and demonstrate it consistently.
For many reps, the data model of CRM is confusing. Accounts, contacts, opportunities, leads, activities—if they’re new to sales, this will be foreign. Even if they’re coming out of a prior sales role, there’s so much muddiness around these things that you can’t rely on existing understanding. So make sure to go through the basic concepts (on the whiteboard) of accounts, how contacts are children of accounts, that an opportunity is a unit of potential commerce with an account, and how activities are used to record information about interactions between sales reps and customers but also as to-dos for future activities.
Show how to create the various objects, and the important fields associated with them—like projected revenue and stage for opportunities, size of total opportunity (size of prize) in an account, contact information and title in contact, and so forth. Cover how to properly disposition items, like marking demo events as held and recording pertinent notes, retiring tasks, and noting closed-won and closed-lost opportunities.
If you have specific reports or dashboards that are key to your reps’ execution, make sure to go through them and ensure that they are sufficiently bookmarked. An example would be Salesforce’s console viewer, which allows for easy task viewing and execution (for to-dos that need action). Examples of key reports could be specific pipeline reports set up so reps can view what opportunities they have open in what stage, or error-checking reports that help reps see open opportunities without sufficient activity, or demos or tasks in unexecuted states.
There are a variety of sales-specific email tools on the market, some of which were covered in prior sections more completely. At TalentBin, we use the Act-On marketing automation suite, and each of our reps has Act-On email integrated directly into Salesforce for templating, open and click tracking, and mass mailing. We also use Yesware for bcc’ing to Salesforce, open and click tracking, and templating integrated directly into Gmail. And we use iHance for catching and pushing to Salesforce inbound emails from prospects.
Whatever the tool chain you have set up, the important concepts to cover with sales-enabled email are bcc’ing to Salesforce for record keeping, templating and mass mailing for efficiency, and open and click tracking for deal insights.
Demonstrate how bcc’ing into your CRM works for ease of recording deal progress, and how email activity is recorded and reported to track rep activity levels. Demonstrate how templates work—why they are there, which ones are available for your team, and how to create new ones, or request that new ones are made. Show how mass mailing works out of Salesforce views, and the pertinent use cases (for instance, sending a targeted “check out this new feature” email to mid-funnel opportunities). Demonstrate open and click tracking, and what it’s good for—for MDRs, that’s seeing how their cold outreach is being received and for account executives, it’s understanding whether follow-up collateral is being engaged with and shared around the prospect organization.
If your organization has invested in sales-specific, or even generic, presentation software, like Zoom, WebEx, join.me, and so forth, make sure you cover common cases. (And if you haven’t invested in presentation software, you should rethink that decision.) At TalentBin, we used ClearSlide, so we covered how to send ClearSlide meeting room credentials via calendar invite or email, how to use the standard slide decks or clone and modify decks, how to execute live screenshares, how to record pitches for later audit or to send to contacts that missed the presentation, and how to execute post-presentation follow-up, like sending instrumented deck hyperlinks to prospects and proper dispositioning of demo notes.
If your organization has power dialing software set up for top-of-funnel activity by market development reps, or mid-funnel follow-up by account executives or account managers, cover the common use cases there as well. At TalentBin, we use InsideSales.com’s PowerDialer to enable our MDRs to quickly cycle through lists of prospects, making calls, leaving pre-recorded voicemails, sending follow-up emails (PowerDialer integrates with Act-On’s emailing), and quickly dispositioning tasks. And our account executives use InsideSales.com’s Click to Call to quickly reach contacts directly from Salesforce and easily disposition tasks and notes directly from that console.
You may have other key sales-specific tools that I haven’t covered, and you’re also not going to be able to handle every single case during training. (Even if you do, your reps won’t retain it; they’ll need to learn through doing.) The important thing is to ensure that your reps understand the goal of each piece of equipment, where it fits in their process, and its key workflows.
While training on tools is important, it’s equally important that new reps understand how and when to use those tools in the sales cycle. Make sure that you fully cover the specifics of your sales organization’s process and cadence.
Different products have different enterprise sales cycles, based on how the typical customer purchases, the size of the average contract value, budgetary cycles, and more. Walk new reps through the sales tempo for your product: How long does it typically take to close a deal? Is it a bottom-up or a top-down sales approach? Or a combination? Who is responsible for what part of the sales cycle? Does market development set appointments, and with whom? Or are account executives responsible for the full cycle? Does a sale typically require multiple presentations, or is it more of a one-call-close sort of cycle? Does it involve trials or pilots? At what point should a rep know that the deal is not going to happen and close the opportunity to make room for more productive uses of time?
Also cover the cadence of your sales organization. Having a solid weekly, monthly, and quarterly cadence is the cornerstone of a grounded, focused team. Whatever your team’s rhythm—meetings, standups, team meetings, pipeline meetings, all-hands, even happy hours—review it, and the goals associated with each get-together.
exampleAt TalentBin, our cadence includes once-weekly hour-long sales team meetings on Mondays to review the previous week’s stats and revenue progress, and to share product and customer success progress, team wins (things they’re stoked on), and learnings (mistakes from the week before to help others avoid); twice-daily standups (just before lunch, and at close of business) to check in on activity, wins and learnings; once-weekly hour-long pipeline meeting to review deals, drive accountability, and get team feedback; a once-monthly company all-hands; and a weekly happy hour at close of business on Friday. And the cycle begins anew after the weekend.
One of the things that I have seen sales organizations really drop the ball on when it comes to onboarding and training is the repetition and practice of key actions. The irony of this, of course, is that sales teams are usually full of former athletes and often analogize themselves to sports teams. But somehow they forget that practice is as important—often more important—than the actual games. Presenting information from slides, even with testing, is not sufficient. No way. Drilling and repetitions, paired sparring, and shadowing are all critical to ensure your reps develop muscle memory before they go live.
The biggest thing your reps are going to need to drill is their demo and presentation. They can (and will) learn on the job, but there’s no reason to burn through actual, valid opportunities as they do so.
During your presentation and demo onboarding, you went through each chapter of the presentation and demo, step by step. Now, have each rep do the same thing. I prefer to do this in the class setting, with each person presenting each chapter of the presentation or demo, and then stopping to get feedback from the instructor (you) and the rest of the team. It’s a slow process—that’s why you only do it once—but it really drills the heck out of the material.
When you’re done with the group drilling and repetitions, split the class up into groups of two for what I refer to as sparring. Time-intensive, per-section drilling is good as a baseline, but after that, it’s going to take a series of mock presentations to really nail the material. I have each pair trade off as presenter and prospect. And while you might think that the individual playing the prospect is really just there as a static foil, it’s actually a very important part of the training; they are being forced to think and react like a prospect—to inhabit the mind of their eventual counterpart in the sales cycle—which will in turn make them a better consultative sales professional. This can be done both with presentations and negotiation calls (account executives) and with pure cold-calling for lead generation (market development reps). And, of course, run your sparring in full “game situation” mode, using whatever tools reps would use in their day-to-day—not sitting in a room looking at each other, but using the phone, presentation software, and so forth, that they will use when facing prospects.
Generally speaking, I’m not a fan of the notion of riding along on calls to learn. This can be done outside of selling hours (or even ahead of onboarding) with recorded calls (as assigned in the pre-work). However, there is something to be said for following along as a full cycle workflow is executed. One of the things we do for onboarding is pair programming, where a new hire is paired for a day with a seasoned individual in their role and follows key workflows in a production-like environment. For market development reps, this would be sitting at the desk with other market development reps as they go shopping for prospects to call, review and execute their tasks for the day, or rip down a calling list, firing off follow-up emails or setting an actual demo. For account executives, a ride-along could be sitting in on an initial or follow-up call or participating in pipeline management and maintenance.
All the training and drilling in the world is great, but when new reps come into contact with live opportunities, it is by no means the time to let up on your onboarding focus.
There are three things I recommend to ensure that all the investment you’ve made to date pays off as the rep goes live: bluebirding, proactive call review, and KPI tracking.
When account executives are just getting started, assign them “bluebird” opportunities—these have a high likelihood of closing. Usually these will be ones that come inbound (through lead-capture forms, which naturally have the highest purchasing intent) and have strong qualification characteristics.
But putting these bluebirds on the rep’s plate isn’t sufficient. Generally, I like to team with reps on early calls, or have another senior rep team with them—not to run the call, but simply to offer backup in the event that they run into something that they don’t think they can handle. Often, the pure availability of backup, coupled with the strong prep to date, makes it unnecessary.
But be sure not to jump into a call if the rep just isn’t hitting messaging at an A+ level; you’re there only in the event that the wheels come off, not to correct slight wobbles. I also find it very helpful for reps to have a printed script of the sales presentation and demo on their desks as they execute calls, even if it’s just the major buckets—not so they can follow along in minute detail, but so they can make sure they don’t miss any key parts. And if they get knocked sideways, they can quickly look down, see where they should be, and regain their footing.
The converse of this strategy is throwaways. There are all manner of leads that will come inbound that are unqualified. In TalentBin’s case, these are organizations that don’t have sufficient technical hiring requirements or don’t have recruiters in-house to do proactive, passive-candidate recruiting. Generally speaking, assigning these unqualified opportunities to a sales rep would be a waste of time, as compared to the other valid opportunities on which they could be working. However, in an onboarding use case, these can be helpful practice demos; the rep knows that it’s not a qualified lead and isn’t under a ton of pressure for fear of losing a potential sale.
This can cut both ways, though, in that it’s important that the rep treat it as a real call—go through discovery and qualification questions and discover that the opportunity is not qualified. In these cases, I recommend that reps offer to do an abbreviated presentation for the prospect, in the event that their situation changes down the road (for instance, they move to an organization more focused on technical recruiting). As you can see, these presentations are an expensive form of practice, as they not only consume rep time that could be spent on valid opportunities, but also occupy the time of a customer that is unlikely to close (it’s not 100% respectful of the client’s time). That said, a few of these can be helpful in getting the rep set up for success.
After these initial bluebirds and throwaways, though, teaming is an extremely expensive form of training and audit, and one that I believe sales managers use far more than they should. It robs sales leaders of time they could spend actually managing—consuming product and program materials, distributing information to teams, building and managing leveraged processes, and auditing and enforcing existing processes. It’s often a form of managerial laziness that masquerades as productivity. However, there are strategies for achieving the goal of call review without the time cost of sitting in on new hire sales calls.
In our organization, we would record all sales calls using ClearSlide’s online presentation system (join.me, WebEx, and others have similar functionality—the modern versions of these are Chorus and Gong). This way, at any point, we can pull a recording and listen to it, after the fact. Even that would be time costly, though, so instead we require reps to surface to the team (at standups) when they’ve had a particularly awesome or particularly heinous call—institutionalizing the practice of sharing. For the awesome calls, we pull the recording and put it in a hall of fame, to be used for future onboarding; for the heinous ones, we discuss them and, if needed, listen to them to see where the wheels came off.
Beyond formal reviews, there are the ambient ones: As a sales manager, you should situate your desk centrally in your org so you can hear what’s going on. Or walk around; take your laptop or smartphone and sit in a different part of the office, listening while you work there. Most of the time, you’ll just go about your normal tasks. But you’ll be attuned to oral distress and pick up any issues, which you can either note for coaching after the fact or address in the moment with a helpful Post-it note dropped on the rep’s desk, pointing out a direction they can think about going. (It’s important to characterize to reps that these are suggestions, and not mandates, lest they become flustered over including something that isn’t relevant if your assumption is wrong.)
These proactive and ambient reviews, coupled with a culture of sharing and learning, will ensure that you catch issues early. Don’t risk leaving them hidden (whether from lack of visibility, or actual obfuscation driven by embarrassment). You’ll see that rep confidence ramps quickly through early wins.
Lastly, as your new hires ramp, you can dial down the amount of high-touch monitoring and coaching and start relying on the core set of KPIs you use to monitor performance across your entire sales team. These would be things like hold rates for demos set by MDRs, win/loss ratios for account executives (although, depending on your sales cycle, this may be a lagging indicator of problems), and signifiers of health or concern at the top of the funnel, like activity levels and stuck opportunities.
While your team cadence should already pick up these indicators of health or distress, take extra time to check in on new reps’ KPIs to make sure they’re tracking correctly. And always cover these, and get rep feedback on how they are actually feeling, in your standard (ideally every-other-week) one-on-one meetings.
One thing about onboarding is that it can feel like when you’re done with it, and a rep or class of reps is up and running and successful, you’re done with the learning and training. While onboarding is the most intensive period of learning and development, ignore ongoing investment in that at your peril. Not only can reps continue to get better with better coaching, it’s key for professional development, retention, and promotion. Further, it’s unlikely that your product and the market will remain static. As your product changes, and the market in which it operates changes, your reps will need to be updated and then tested on this new information, so they can be just as sharp as when they exited onboarding, however many months or years ago.
Just like you had a structured calendar for onboarding reps, whether SDRs, AEs, or AMs, you’ll want to do the same for ongoing learning and development. At TalentBin, we had an hour blocked at the end of the day on Friday that was specifically for this. SDRs took the time to do drilling with their management and each other to work on objection handling, messaging review, or demo practice (which wasn’t something that was important for their day-to-day, but was part of professional development, and had the added benefit of making them more confident and competent in their prospect-facing interactions, regardless). AEs would use this time to work with their managers and teammates on different parts of their sales motions, whether it was discovery, presentation, objection handling, negotiation, and so on. But the important part was that the time was on the calendar, and as such, would be prioritized.
Ensuring that this time is well used is particularly important for SDRs. The ability to hire, onboard, and train up SDRs to the point where they can be revenue-generating AEs is an extremely valuable skill for an organization to have. It’s a sort of enterprise value sales alchemy, where through smart recruiting, onboarding, and training, you can turn copper into silver into gold. This also keeps your cost of hire and sales down, in that you’ll have a machine manufacturing fully functional junior reps, rather than having to bid at existing reps at benchmark organizations. And your investment in SDR professional development will pay dividends.
It’s highly unlikely that your product will stay static for very long, which means that it’s important that your reps are able to present it and all its latest features in a way that reflects its current state. And the market is continually changing, with competitors making their own moves, and incumbents reacting. All of this means that when something occurs that extends or modifies the information that reps learn in onboarding, you will want to bring them up to speed.
With new releases, a good way to ensure the sales team is up-to-date is to embed new product updates into part of a cadenced meeting. If you have a weekly sales team meeting, having product management or product marketing participate for ten minutes of that meeting to give a review of what just shipped and what’s on deck, can help start that information soaking into your reps’ brains. That likely won’t be sufficient, so additionally consider having one-off training exercises built around new releases. If you ship a big new feature, and you’ve built some new slides for the sales deck, and would like to add some messaging for it to the sales demo, then make sure that you have that information documented. Then you can either schedule a special event—maybe it’s during a catered lunch—or choose to take over the hour that you have scheduled weekly for training and professional development for this.
So too with market changes. If a competitor does something that meaningfully impacts how you position or present your product, treat it like a product release, but instead, it was the market that released new features of its own that changes how your product is viewed. The point is these product and market changes won’t just naturally be consumed and understood by your reps, and rather than having their understanding of your product and market frozen in amber from the point at which they were onboarded, you want them at the vanguard of knowledge both regarding your product and the market.
As noted at the beginning of this chapter, the biggest cost to a young sales organization that has hit product-market fit and is now scaling is the opportunity cost of missed or delayed sales. Rigorous, thoughtful onboarding will minimize these costs; engender a positive feedback loop, faster time to revenue for new reps, and higher retention (making your recruiters very happy, or minimizing recruiting agency costs); and enhance team cohesion and excellence.
When onboarding is done right, it’s just a good scene, all the way around.
Hiring, Onboarding, and Ramping Salespeople (Cory Bray and Hilmon Sorey)
The Sales Acceleration Formula (Mark Roberge)
The Sales Enablement Playbook (Cory Bray and Hilmon Sorey)
Leading Sales Development (Alea Homison and Jeremey Donovan)
The Sales Development Playbook (Trish Bertuzzi)
At the beginning of this book, I told you that your go-to-market would have two stages: First, you would need to figure out how to sell your offering (the approaches for which were discussed in the first two-thirds of the book). Then, you’d begin to scale that up (which is what the last part of the book was about).
If you are now successfully scaling up, then congratulations! You’ve moved beyond the province of this book. You are now a bona fide sales professional. And if you have a set of sellers reporting to you—successfully closing business—then guess what? You are now a sales leader. Way to go!