Sales Onboarding 101

25 minutes, 3 links


Updated August 22, 2022

You’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.

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.”

Standard Administrative Work

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.

Cultural Onboarding

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:

  1. You don’t have to be an engineer to operate with an engineering mindset.

  2. We are the product managers of our sales organization.

  3. 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.

Your organization may share these tenets, or you may have your own. But the important thing is to proactively state them as a baseline during your onboarding process.

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.

Business and Market Subject Matter Onboarding

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.

Market 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.

Business Driver Understanding

Relatedly, you also want to ensure that your staff understands the key business drivers that your solution is addressing. How does your client’s business work, what are the key cost and revenue levers, and how do solutions covered in the market review impact them? How does this calculus change for different segments or verticals that you address? What are the common metrics by which these business drivers are measured? And where does your solution fit into this puzzle (more on this later in the detailed product training)?

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.

Technical Understanding

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.

Product and Presentation Onboarding

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.

Initial Product Walk-Through

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.

Sales Presentation and Segments

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.)

Customer-Facing Demo and Demo Segments

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.

Objection Handling

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.

Tools and Process Onboarding

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, 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.

Provisioning and Configuration

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