Action-Focused Onboarding
- Mike Pinkel
- Mar 24
- 14 min read
Updated: 2 days ago
The traditional startup sales onboarding process can be summarized in three words: sink or swim.
I saw this up close in my first few sales jobs: new AEs joined and did their best to learn from the current team.
Some never learned and failed. Those that succeeded took extra time to get up to speed because they had to figure it out mostly on their own.
Startups face a lot of risks that are partly out of their hands. Teams accept the chance that fortune might not smile upon them.
But let's be clear: If you fail because you hired good AEs and then abandoned them, that's on you.
This article will give you practical methods for onboarding AEs based on what worked for me building the Coursera Mid-Market Team.
Onboarding was key to our team’s success. We continuously had to hire more reps as our team grew and as the best reps got promoted to the enterprise team. We couldn't rely on new AEs knowing what to do; our target hire was an early-career salesperson.
I needed a way to rapidly take talented early-career sales reps and make them effective.
I did that through action-focused onboarding: Having reps practice the conversations that solve the most important sales challenges they’ll face in the field.
In this article, I'll show you how to make that happen. We'll cover the following topics:
Why Onboarding Matters
Let's be honest: Many early-stage companies don't devote many resources to onboarding because they don't think it's worth it. They have many calls on their time; why should onboarding get to the top of the list?
Because it drives two key factors for sales success: shortening the ramp time that it takes for sales reps to become productive after being hired and increasing the percentage of sales reps that succeed.
Why? Reps with proper support learn faster and there are reps out there who can sell but won't figure it out on their own.
Ok ok, but is it worth the effort?
Yes. Let's run two estimates: one where onboarding shortens ramp time and increases the success percentage (our "robust estimate") and one where all it does is shorten ramp time (our "modest estimate").
In the robust estimate, onboarding could make or break your year. In the modest estimate, it's more than worth the effort.
Robust Estimate
Imagine two SaaS companies hiring their first substantial batch of AEs. Company 1 invests in solid onboarding, Company 2 doesn't.
Let's keep the math simple: Both hire four reps with million dollar quotas in January. Their reps either succeed and hit quota after their ramp period or don't and never sell anything.
For our robust estimate, we'll assume that onboarding makes one more rep succeed and shortens ramp by one month. Company 1 gets three of four reps to succeed after a four month ramp. Company 2 only gets two reps to succeed after a five month ramp.
The gain from onboarding is over $800,000. That could make or break the year for an early-stage company.
The chart below summarizes the numbers (click on the graphic to expand it if you want to look closely):
Modest Estimate
What if onboarding helps but not THAT much?
For our modest estimate, let's assume that onboarding shortens ramp time by one month and that's it. Both companies have three out of four reps succeed, but Company 1's reps have a four month ramp versus five months for Company 2.
That gain from onboarding is $250,000 from good onboarding, more than enough to justify the effort.
The chart below summarizes the numbers (click on the graphic to expand it if you want to look closely):
Define the Core Sales Challenges
So how do we create good sales onboarding?
After all, there are plenty of companies that have created sales onboarding only to see it have little effect.
The first step is to define your core sales challenges. These are the critical hurdles that your best reps overcome to sell more deals, faster deals, and larger deals.
Why start by defining challenges?
If you just tell your reps to go practice “doing a demo,” they’ll learn to click on buttons in the product and that’s about it. But if you confront them with a scenario that presents your core sales challenges and ask them to do a demo that addresses those challenges, they’ll learn to do a demo that closes business.
Aim for two or three core sales challenges; no more than four or five. Not every significant subject can make the list. That’s OK; you can cover the subjects that don’t make the cut later on with other onboarding resources like e-learning.
Great onboarding exercises require richly defined challenges. To get you started, here are the two core challenges we addressed for the Coursera Mid-Market Team:
1. Proving Value
Ok ok, it's not a revelation that proving value was a core challenge for us. The key was the exact form that this challenge took.
We were a premium provider in the online learning space.
Online learning isn’t like enterprise resource planning software: Your company won’t collapse tomorrow if you don’t have it.
Uncovering customer needs was therefore key: Prospects who didn’t see any need wouldn’t buy online learning at all; prospects who didn’t see a strong need would buy a lower cost provider to “check the box.”
Competition was also critical: Most prospects would be considering us alongside other providers. Showing that we matched the prospect's needs was great, but we really needed to show why we matched them better than alternatives.
Finally, we had to tie our value to specific use cases within the prospect's company. Customer's didn't just buy our product, they bought it with specific user groups in mind. We sold bigger deals when we proved that we fit more use cases and user groups.
2. Crafting a Matching Commercial Proposal
It's also not a revelation that our proposals aimed to get deals closed and to incentivize larger deals. The useful part was to define exactly what made this challenging for a typical prospect.
Different groups of users got different levels of value out of our product. There were usually power users who would use the product a lot and get a lot of value from it, medium users who would use the product consistently and get solid value out of it, and other users whose usage was unknown.
If we set the price too high, we would be stuck with a small deal. The customer would buy only for their power users because only their usage justified paying a high per-person price. This left value on the table for both parties: They got less value because fewer employees could use our product and we got less revenue from a smaller deal.
Sales reps therefore had to design commercial terms that made it a fit to cover all of these user groups while staying within our pricing guidelines.
Create a Hypothetical Prospect
The next step is to create a hypothetical prospective customer that presents the core sales sales challenges. Your onboarding exercises will relate to this hypothetical prospect, giving new AEs a chance to practice the key elements of a full sales process. Make the hypothetical customer fit your ideal customer profile so that new AEs learn to sell to your best prospects.
We created a medium-sized tech company for our hypothetical prospect at Coursera; that was our ICP. We based it on the grocery delivery company Instacart. Starting with a real company gave us a head start in imagining how our core sales challenges might apply to our hypothetical customer.
Next, we gave our reimagined "Instacart" a backstory that included our two core sales challenges:
1. Proving Value: We imagined some general business problems that learning could solve and how those might apply to different groups of employees at Instacart. We then inserted some of our most common competitors into the mix so our AEs would have to show why our product was better in the context of those business problems.
2. Matching Commercial Proposal: We invented three user groups, each of which had different needs and employee counts. This created a puzzle for our AEs: There was a way to craft a win-win proposal to work with the whole company, but the sales rep had to figure out how to structure the deal to make that happen while staying within our pricing guidelines.
Put it all together and we had a bread and butter deal for our team: Reps who could solve these challenges for this kind of prospect could sell our product.
Build Simulated Sales Conversations
Next, build three to five simulated sales conversations that relate to the hypothetical prospect. Choose conversations that are both common in your sales process and challenging to execute well.
You’ll create a one page set of instructions for each conversation that explains the purpose of the exercise, tells the AE exactly what they are going to do, and identifies the resources they need to consult as they prepare. Most of the resources will be things you’ve already created (or at least should have created!).
These are the three simulated conversations that we used at Coursera:
1. Discovery/Overview Presentation
This gave reps a chance to practice uncovering needs and giving an overview of how we’d address them. They’d ask discovery questions, present a slide deck, and close to next steps.
The best reps would uncover several layers of information about the prospect’s problems, give a clear pitch, incorporate what they’d learned in discovery into their pitch, and highlight key differences between us and the competition.
The proctor administering the exercise (usually me) would play the role of a manager at the hypothetical prospect. I’d ask typical questions and be ready with information from the hypothetical prospect’s backstory that I could share if the AE asked good discovery questions.
These were some of the resources we used in the exercise:
A recorded training on discovery/initial pitch calls
Call recordings of real calls
A pitch deck
Those of you who are P.S.I. Selling fans will recognize this exercise from the mock pitch portion of The Hidden-Gem Hiring Process – you can and should use the same scenario for both hiring and onboarding!
For more on great discovery, check out our article on effective discovery.
2. Software Demonstration
This gave reps a chance to show how the product solved the prospect’s problems using the information they’d learned during the discovery/overview presentation. They’d summarize the main points they wanted to make, demo the platform, answer questions, and close to next steps.
The best reps would adapt the main points they wanted to make to the facts they’d learned about the prospect, tie the product components they were demoing to the main points they identified, and talk about how those components were different from competitors.
These main points were contained in a set of Summary Slides that gave an overview of the Problems we solved, the Solutions we offered, and the Impacts we delivered (P - S - I - hence P.S.I. Selling). The best reps would update the Summary Slides to incorporate what they'd learned in the discovery/overview presentation.
The proctor would ask questions off of our product FAQ during the demo and ask how we were different from competitors.
These were some of the resources we used in the exercise:
A recorded training on demos
Call recordings of real demos
A product FAQ
A competitive analysis of us vs. others in our space
For more on great demos, check out our article on demoing with structure and impact.
3. Proposal Presentation
There were two parts to the proposal presentation: (1) formulating pricing and (2) presenting a proposal.
In the first part, the AE would meet with me to share the pricing options they wanted to propose. I’d be the real me – I wouldn’t be pretending to be a manager at the hypothetical prospective customer – and I’d give them feedback on their pricing options.
The best reps came up with pricing that incentivized a larger deal and could explain the reasoning they’d used to get there.
In the second part, the AE would present their proposal and the proctor would play the role of a manager at the hypothetical prospective customer.
The AE would provide an overview of the value of our product in the hypothetical customer’s situation using Summary Slides (updated again after the demo), explain how our pricing worked, advocate for their preferred engagement option, and align on the process for getting the deal completed.
The best reps proved value specific to the prospect, summarized why we were a better choice than competitors, explained why our pricing was fair, and made a strong business case for the purchase option that the rep was recommending (usually a large purchase!).
These were some of the resources we used in the exercise:
A recorded training on proposal presentations
Call recordings of real proposal presentations
Guidelines on what pricing was allowed and what pricing made sense
A negotiation strategy spreadsheet that allowed them to easily play around with different pricing options
A template proposal
For more on proposals, check out these tips.
Implement the Plan
The final step is to create a schedule for the onboarding activities and decide who is responsible for executing each component. The way you plan onboarding depends partly on the resources you have, so let’s start by identifying the biggest potential force multiplier: mentors.
Mentors
Having a mentor plan means asking your proven AEs to take a role in helping the new AEs get up to speed.
Almost every sales team should have mentors play some role in onboarding. The modest way to do this means giving every new AE a mentor who serves as a buddy and a first point of contact for questions. This helps the new AE spend less time spinning their wheels, gets them socially integrated, and gives them a second perspective on what works at your company.
You should also consider having a robust mentor program in which the mentor is a key actor in implementing the onboarding plan and rides shotgun for some of the new AE’s early calls.
How do you choose which kind of program to use? Robust programs make sense if you're hiring a lot of new AEs, you’re currently highly leveraged with many direct reports, and/or you’re new to the company yourself. In these situations, your time is limited and your new AE would benefit a lot from having another resource.
If you opt for a robust mentoring program, be sure it’s a win-win deal for mentors. Mentoring imposes costs on your AEs. After all, they're paid on commission. Time mentoring is time away from selling and growing the sales team means less territory and fewer leads for existing AEs.
Don't gloss over this; your mentors are your best AEs and you need to treat them with the respect they deserve.
Here are two potential wins for mentors: First, mentoring could set up career growth by being a kind of leadership training experience that sets them up for management roles or for promotion to a more senior team that works on larger accounts. Second, you could offer a cash bonus, akin to a SPIFF. Explicit wins like these are all the more important if you’re new to the company and didn’t personally train the mentors.
The Schedule
So how do you arrange all these activities in a sensible way? Create a schedule!
Don't wait for new AEs to complete onboarding before they start selling; instead have onboarding get them ready to start taking leads ASAP by training them to handle the beginning of the sales process first. Onboarding and selling happen at the same time, with onboarding staying a few steps ahead of where the new AE is likely to be in their deals.
Here’s an example onboarding schedule that features a robust mentor program. This doesn't include every onboarding element (you might add things like company specific e-learning) but it shows you how the main elements might play out.
Week 1: Welcome
This week is all about getting set up. The rep should meet the team, get logins for their software platforms, get their territory, and observe all of their mentor’s sales calls.
The rep should also review all of the resources for discovery/overview presentations so they’re ready to start the exercises early next week.
Week 2: Discovery/Overview Presentation and Territory Planning
The rep should conduct three simulated discovery/overview presentations: 1x with the manager and mentor, 1x with the mentor, and 1x with the manager (mentor optional). The first run generates initial feedback, the second gives the rep a chance to practice that feedback, the third is the manager’s chance to certify the new rep on discovery/overview presentations.
The rep should also complete a territory plan this week identifying their pipeline strategy, key target existing accounts they want to grow, and key target new business accounts. They should continue observing all of their mentor’s calls and as well as calls by other members of the team.
They should also review the resources for software demos so they’re ready to start the exercises early next week.
Week 3: Selling, Software Demonstration, and Prospecting
The rep starts selling this week, including prospecting and taking inbound leads. They’re ready to execute the first part of the sales process because they’re certified on discovery/overview presentations.
The rep should conduct three simulated demos: 1x with the manager and mentor, 1x with the mentor, and 1x with the manager (mentor optional). As before, the first run generates initial feedback, the second gives the rep a chance to practice that feedback, the third is the manager’s chance to certify the new rep on software demos.
They should continue observing all of their mentor’s calls and as well as calls by other members of the team. They should also review the resources for proposals if they have time.
The rep should lead their own calls but have either the manager or the mentor ride shotgun.
Week 4: Catch Up
It’s good to build in some catch up time into the onboarding process so that reps can come back and complete anything that’s slipped. Calendars get cluttered, people are out of town etc.
The rep should continue observing all of their mentor’s calls and as well as calls by other members of the team. They should also review the resources for proposals if they haven’t already.
It’s also a good time for them to get some initial feedback from their mentor on their prospecting work. What’s going well, what’s not? What could they do differently?
The rep should lead their own calls but have either the manager or the mentor ride shotgun.
Week 5: Proposal Presentation
The rep should start the week by meeting with their manager to share their proposed pricing and to discuss how they arrived at it. If their pricing checks out, they can proceed to the proposal presentation.
The rep should conduct three proposal presentations: 1x with the manager and mentor, 1x with the mentor, and 1x with the manager (mentor optional). As before, the first run generates initial feedback, the second gives the rep a chance to practice that feedback, the third is the manager’s chance to certify the new rep on proposal presentations.
The rep should continue observing all of their mentor’s calls and as well as calls by other members of the team.
The rep should lead their own calls but have either the manager or the mentor ride shotgun.
Week 6: Catch Up
This is the final catch up week and the last week of onboarding. The week before this one was pretty full so it’s totally OK if a few things have slid into Week 6.
The rep should continue observing all of their mentor’s calls and as well as calls by other members of the team.
The rep should lead their own calls but have either the manager or the mentor ride shotgun.
At the end of this week, you have an AE who is ready to fly solo and bring in some great revenue. Congrats!
The Takeaway
Many early-stage sales teams don’t want to invest in onboarding until they’ve grown to $10 million in ARR or more. It seems like an established company thing to do.
But not investing in onboarding until you become an established company lowers the odds that you’ll ever become one.
Effective onboarding should be action-focused, giving reps a chance to practice solving the challenges they’ll solve with real deals. It takes planning, but even small teams with limited resources can do it well.
You owe it to your team and your company to make it happen.
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If you liked this article, check out our article on Guerrilla Sales Enablement to see how to build the resources your team will need for success. You can also check out the P.S.I. Selling Content Page for more insights on sales communication, strategy, and leadership.
Want to build a sales process that proves value and a team that can execute? Get in touch.
For more about the author, check out Mike's bio.
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