How to onboard your sales team

Onboarding sellers is very difficult because your product and processes constantly change over time

When I worked at Slack, I was responsible for building & running the first iteration of our sales bootcamp to onboard new members of the sales & customer success team.

Everyone probably knows this intuitively, but onboarding is a bit of a drag for pretty much everyone involved. To a certain extent, there is no way for onboarding not to be painful, the same way that building muscle in the gym must be painful, by definition.

Whenever you build a new muscle, it’s going to hurt- and learning how to sell a brand new product is to build new muscles no matter how experienced a seller you are.

In this edition of EarlyGTM, we’re going to explore an approach to make sales onboarding less painful for both parties- for existing team members (who don’t want to teach the same stuff over and over, and also can’t spend unlimited time building an infinite amount of onboarding content) and for the new hires (who very rarely have a superb onboarding experience, and are anxious master their craft so they can make as much money as possible, as quickly as possible.)

TL;DR - turn onboarding into a quarter-long, self guided project with clear deliverables, guidelines & milestones

To keep things simple, the key to sales onboarding is to focus first and foremost on asking your new hires to pull answers from the current team, as opposed to spending a ton of time and energy creating new content (which will become more and more outdated every single quarter.)

You can then gradually add a content library to this foundation over time, because writing a ton of content up front is virtually impossible for a lean team.

Each week of onboarding should conclude with a presentation, live activity, or some other kind of test where the new hire must synthesize a week’s worth of knowledge, divided into key themes and topics. This approach takes most of the heavy lifting off of the sales manager and/or sales org, and places the lifting onto the seller in a way that makes sense for everyone involved.

A new seller simply can’t learn their new role without heavy lifting. In contrast, a manager’s heavy lifting should be kept as minimal as possible given their workload.

This project-based approach also provides the new seller with some legitimate skin in the game. Taking a bunch of tests and courses that no one reads, grades, saves, or cares about is a very low skin in the game, highly wasteful activity. Asking the new seller to present to their manager each week, in a way that allows the manager to naturally share insight and feedback, is a high skin in the game activity.

If you, as the new seller, don’t perform well in this system, your manager will know that you’re not taking your onboarding seriously- which will definitely hurt ramp time and in turn, the company’s ability to hit long term goals.

Break each week into a theme

The following template may not work exactly the same for every sales org, but will at least serve as a universally applicable starting point:

Week 1: Understanding the product(s) you sell

Week 2: Understanding the sales process at your company

Week 3: Generating opportunities

Week 4: Discovery

Week 5: Personas

Week 6: Product Demo

Week 7: Pricing, Products, and ROI

Week 8: Closing deals & post-sale

Week 9: Territory plan & final sales certification

(Obviously, feel free to adjust these as needed.)

Additionally, if you (as the sales leader or early executive) can write a short article, or maintain a continuous wiki with relevant links around each of these topics, your new sellers will have a solid starting point instead of hunting each and every topic from scratch. Short articles with a lot of links are better because they are easier to produce, easier to maintain, and easier to read through as a new hire.

Organize each week into an activity, led by the new seller, to present to their manager each Friday

By the end of each week, your seller should present either a deck or bulleted, well-organized GDoc that forces them to spend time focused on each weekly topic. As a manager, you should schedule time each Friday to review these activities with your new seller(s). Or equally viable, ask them to find an hour on your schedule each Friday for the next 9 Fridays- the manager should be saving their time, energy and focus for the highest leverage onboarding activities.

As a quick note, appearance & imagery for these decks isn’t super important. Sellers shouldn’t be responsible for making beautiful decks, but it is a useful skill to practice synthesizing your thinking in a clear, concise, and sequential way.

Another note: advise your sellers to be diligent about linking to reference docs (ie- pricing guides, key wikis, links to key decks, etc) in their work- remind them that collecting these links will come in handy later. Ultimately, your sellers are building these presentations for their own direct benefit.

Month 1

Again, goes without saying, but please adjust the following as needed- these are quick, universally applicable jumping off points that should ideally be customized.

Week 1 Presentation: build and present a deck explaining the most important features of our product, ranked in order. This is purely based on opinion- so your list should differ from anyone else onboarding alongside you. Additionally- what features are important, but didn’t make the top 5? Why?

Week 2 Presentation: build and present a GDoc explaining the sales cycle at (Insert Company.) What makes our sales cycle different from the last company you worked for? What are the key steps and milestones in our sales cycle?

Week 3 Presentation: build and present a GDoc explaining how you plan to generate opportunities. How does our balance of lead gen differ from the last company you worked for?

Week 4 Presentation: build and present a deck explaining your personal discovery process. Is it consistent with the discovery process this new org you just joined uses?

If your sales team uses call recording software, listening to calls should be a big part of this prep process. If not, the new seller should join as many live calls as a shadow as they can.

Month 2

Week 5 Presentation: build and present a deck explaining our sales personas. What personas do we sell to? What products does each persona care about? Which personas bought our biggest deals? What are those deals, and who sold them?

Week 6 Presentation: build a sales deck (typically called a “first call deck” even though it’s actually a demo deck) based on what you’ve seen from your peers, present that deck with a real company and real person in mind, and lead a product demo of our product.

Week 7 Presentation: take the real company and real person you built your demo presentation around last week, and present 3 different pricing options to them based on their company size and perceived need.

Week 8 Presentation: build a GDoc (with screenshots) explaining the steps needed to close a deal to CLOSED WON in Salesforce. What happens after you change the deal to closed won? How does the deployment handoff process work?

Week 9 Presentation: in order to graduate from “sales onboarding” present your territory plan for how you’re going to approach hitting your number in your first quarter post ramp.

Notice if you will that every single one of these docs will come in handy as reference points as the seller starts to do their job.

Principles of this approach

1. These activities should not feel like busywork. The seller should always see the “what’s in it for them” benefit of each activity, which is to learn their new product, and the steps of their new sales cycle. These decks and docs don’t have to be long, they should just be thoughtful and based on real digging.

2. It’s better for new sellers to search for, find, and build their own content (which by definition, will always come from up to date information if they have to search for it) than the org building content that will constantly become out of date. Also, your sellers reading a bunch of massive, perfectly written articles or wikis will typically not lead to strong recollection- most sellers learn by doing and not reading.

3. As your org grows, you can and should start to schedule live classes taught by your existing team. Because your new sellers are focused on doing a good job for their end of week activity, they can ask better questions, focus on pulling key information they need to complete their activity, and they will feel much more engaged and focused because the classes serve to help them reach a tangible goal (ie- look smart in front of a manager at the end of the week.)

4. Your existing team should make themselves available to help sellers with these activities. It’s a much lower lift for your team to be helpful to new sellers, equipped with knowledge of what they need to achieve, than to map out every single piece of data before they begin, and expect them to read and remember it all

5. End of week presentations work well because a sales manager doesn’t have to spend any time prepping, or any time grading something after the fact. You can just watch the presentation, see where your seller is development-wise, understand their strengths and weaknesses, understand progress, and coach and discuss in the moment. The problem with startup onboarding is that every manager, leader, and exec is absurdly busy, and the problem never gets better over time.

   Managers should optimize for the most important, high leverage activities, which is course correcting after a seller has a chance to do work on their own.

6. Remember, most content, processes, product explanations, etc. will change over time. As time goes on, your team may want to build official content, eLearning, and live courses around each of these topics. Because your product and feature set will always evolve, try to link these courses you build to wikis that are going to be updated and maintained by the team, as opposed to static content that no one updates.

7. I’ve found that activities that need to be graded after the fact don’t work well. I’ve also found that activities that require self recording don’t work well either. Managers have to be hyper-realistic about their priorities- grading papers or watching videos is typically too boring for a manager to prioritize.

8. This approach also forces sellers to watch existing calls, spend time with their teammates, and rely on their teammates to find answers. Most answers in a sales org day-to-day reside with teammates. Sales orgs are dynamically evolving organisms, so your sales onboarding design must align with that reality.

9. Collaboration with fellow onboarding sellers and teammates should be encouraged. Just make sure that a seller actually understands the content they’re building- if they totally copy someone else’s work, they aren’t learning, and won’t be able to answer your follow up questions effectively.

10. First impressions are really important, on both sides. Try to make day one as special for your new sellers as possible. In return, if you’re a new seller reading this, you should do everything you can to inspire confidence in your managers that they made a great hire.
    
    Managers typically notice if a seller is ramping slowly, or isn’t taking onboarding seriously, and that’s not a great situation for anyone.

Tips for your new sellers’ first day & first week on the job

• your new seller’s calendar should be relatively full- the idle mind of a new hire is not a good thing

• you should make sure to spend as much time as you can day 1, week 1, month 1 with your new seller. You want your new hire to be as excited about their new job as possible, and don’t want them thinking “did I make a mistake coming here?” Losing a new hire prematurely, or failing to ramp a new seller correctly, is very costly.

• arrange for your new sellers to meet a some of their teammates day 1- a sense of belonging is powerful

• arrange for your new seller to have an onboarding buddy, responsible for their onboarding success. Ideally, your best sellers are assuming this mentorship role, and also aren’t the lone wolves on your team.

• communicate the onboarding plan to your seller on day 1. Sellers want to know that there’s a plan. As soon as your new seller has their onboarding plan, they can start focusing their attention on finding and mastering the material they’ll need to be successful.

• The best motivation for a seller is the opportunity to be successful in their role and crush their quota- virtually nothing else matters. Onboarding should be oriented towards that and that alone- it should never feel oppressive or unnecessary.
  
  If needed, explain the “why” behind this type of onboarding program, which is that it’s better to motivate sellers to find answers on their own then to just read a million (likely out of date, impossible to keep current) articles.

• Try to set onboarding expectations realistically with your new seller. If sellers know what is expected of them, if they know that they will not be bombarded with a bunch of boring reading, and if they know exactly how they will be measured as they onboard, they will be much happier and more comfortable.

Summary

Sales onboarding is really difficult to get right. The most productive people in your sales org need to spend their time on their core job, they don’t have a ton of time to onboard new people.

But at the same time, if you don’t find a way to successfully onboard new people, your org will never scale. Making onboarding even more difficult, your product and processes will change constantly, meaning: very few onboarding courses or resources will survive over time without being intentional.

(Note on an additional challenge: even if you have the luxury to hire someone solely focused on sales onboarding, that person will never be as skilled at relevant sales skills as an active sales manager, or a current top seller.)

I believe the solution is self directed learning, where managers optimize for providing a clear guideline for the end of each week deliverable. Ideally, managers can augment these activities by building in-person learning, wikis, resources, articles, tests, quizzes, etc. around that core.

As soon as you can (as a sales manager or early stage exec) you should add live courses taught by current team members that directly align with new hires reaching their end of week goals. End of week goals in the form of presentations will create more engagement, provide more motivation, and require less maintenance than the old way.

Shoutouts to:

Nikki Curtis and Bradford Jordan - who were hugely influential teachers as we built a similar program at Slack. Two of the best in the business.

Thanks for reading EarlyGTM post #8!

Mike Marg
Principal, Craft Ventures

(for more thoughts on go to market, and occasional sports-related frustration - @mikemarg_ on Twitter)

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