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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.
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.