How to onboard your first sales rep

A lot of founders want to get out of founder-led sales.

I get it, you launched your startup because you like to build. You like to pursue your grand vision.

All of that stuff is important. But selling (or figuring out how your company will make money) will always be your core job.

Once you’ve figured out enough of the sales motion, you can start hiring your first reps. Once you have a couple successful reps, you can look at hiring your first sales leader.

Takes a while to get there. You’ll have a lot of battle scars, but it’s important you figure it out.

Because you need to know a lot about how you win deals in order to teach someone to be successful.

And you need to figure out a process that’s teachable - not your founder-magic charm. Or you’ll never be able to make the successful leap from you being the first sales rep to having a successful sales team.

This is where most founders get stuck in their founder-led sales journey. They’re winning deals, but not sure why. They can sell as the founder, but they tried hiring a rep before and they failed.

In this newsletter, I’ll break down how I’ve successfully onboarding 100s of sellers into SaaS startups and scale-ups. And what you ABSOLUTELY need in place for them to be successful.

Without this, they will struggle. They’ll be frustrated. You’ll be frustrated. Nobody will have a good time.

Here we go.

Table of Contents

• The formula for sales onboarding

• Documented Playbook

  • Market Knowledge

  • Customer Knowledge

  • Product Knowledge

  • Sales Knowledge

• Library of successful sales cycles

• Reverse-engineer your time to X

• Where ramping a sales rep fails (Math)

• Warning to founders

The formula for sales onboarding

There are three things you need in place in order to successfully ramp up a sales rep:

1. A documented playbook

2. A library of calls and follow-up emails for successful deals

3. A reverse-engineered time to X structure

When you have these 3 things, you can start mapping out an onboarding plan for your sales rep.

Let’s break it down.

Documented Playbook

The playbook formula for onboarding goes like this:

Market Knowledge → Customer Knowledge → Product Knowledge → Sales Knowledge

Market Knowledge

This is the space you operate in. CRM, quote-to-cash, productivity, sales engagement, payment software, etc.

It’s important to get a broad understanding of the market and why it exists. Who are the major players, how has the market evolved over time, where’s the untapped opportunity.

Usually you can pull free market reports on this (I would even run a ChatGPT Deep Research report on a few key elements of the market).

This will give the sales rep a good frame of reference for what this category of tools/software/apps/services does for prospects.

Customer Knowledge

Here’s where you should spend the bulk of your time in the first week of onboarding a new sales rep.

In your playbook, you want details about the types of companies you work with. The personas you work with. Their jobs-to-be-done. The workflows they currently deploy. The challenges/pains/problems that come with deploying those workflows. What they’re trying to accomplish.

(If you know the FOUNDER framework, you can already start picking out a pattern here).

You want to model this on your best customers. It’s OK to share case studies, g2 reviews, interviews, etc. here. I’d also layer in a bunch of discovery calls that you’ve done where the prospect clearly articulates their problems.

This section of your playbook should be highly pain-driven. Pain closes deals. So you need to make this clear.

Product Knowledge

For this part of the playbook, you want to outline general capabilities and useful workflows of your product.

This should not be a deep dive into every nuances, features, functionality. For sure not in the onboarding phase (maybe once they’re with you for a couple years).

Do not make onboarding a firehose of product info.

For those founders who’ve worked with me, they understand how important it is to hold back on showing product in order to be able to successfully close deals.

The sales process should be about understanding the prospect, not showing off your stuff.

So in order to make sure the sales rep doesn’t jump into bad habits of showing everything, you want to limit this section to the main workflows, capabilities, and product objections that are typically shown in the bulk of your sales cycles.

Then you want to map those workflows and product capabilities to the pains they learned in the “Customer Knowledge” part of your onboarding. Workflows always need to map to pain, because that’s how they’ll eventually demo.

If they don’t know an answer, that’s OK. Sales reps understand that they can pull in a resource (like you as the founder) into a second call to do a deeper dive demo. That’s OK.

They need functional knowledge of the product so they can answer questions and do a v1 demo. That’s all they need for onboarding.

Sales Knowledge

In this section of your playbook, you are giving them every play possible to get a deal to closed:won.

Should include:

• Your ICP/personas for targeting

• Key messaging for emails, LI DMs, and cold calls

• Qualification questions

• Discovery framework

• Objection handles

• Key customer success stories (mapped to pain+capabilities)

• Your sales stages in your CRM

  • What each stage means

  • What happens during each stage

  • What you need to complete in order to move something forward

  • What the prospect needs to complete in order to move something forward

  • Possible next steps for each stage

• Key calls during the sales process

  • How to structure and run the calls

    • Kickoff scripts for each call types

• Demo framework

  • Key chapters to show

  • Scripts and mouse movements for each chapters

• Follow-up framework

  • Call summary email template

  • Professional accountability follow-ups

  • Multi-threading

  • Gone-dark play

• Quoting/proposal process

• Contracting process

• CS/Onboarding/Implementation process for handoffs

• Any additional tactical plays that you’ve documented

Library of successful sales cycles

If you’re not recording calls and logging your emails somewhere, start now. You need to be able to show a sales rep what good looks like. The fastest way to get there is to show them exactly how you’ve run sales cycles in the past.

For your library, you want to organize it by deals won. You can also organize it by segments if you sell to multiple segments (example: verticals/industries, use cases, personas, SMB vs MM vs Ent).

You can organize this in a spreadsheet if you want, or if you use a fancy tool like Gong you’ll be able to save libraries this way.

Each row would be a deal that you’ve won, and should have the following:

• You should link to the deal in your CRM with all of the FOUNDER fields filled out.

• You should link to every call that happened in the sales cycle, in sequential order.

• You should link to all of the follow-up emails (at least the summary emails after the calls), and any important interaction.

• You should add notes to the opportunity around challenges/obstacles you overcame, how you moved the deal forward, what was your thought process throughout the deal, etc. Explain your thinking and actions you took to get it to closed won.

Have your reps go through entire sales cycles. It really puts the whole sales process in perspective.

Often I see founders make the mistake of just giving them discovery calls - that’s good for the “Customer Knowledge” part of onboarding, but it won’t teach a rep how to get from intro to close.

Reverse-engineer your time to X

Now that you’ve documented everything possible that your sales rep will need in order to understand how to do the job well, you need to figure out their ramp time.

Everyone gets this wrong at first. Your sales rep will need much more time to ramp than you think. So set your expectations right.

But you need a way to gauge if they’re on the right track early - because if they’re not, it is INSANELY expensive to keep an underperforming sales rep on staff that will never “get there.” I’ve made this mistake plenty of times. Eventually I could tell by week 4 if someone would make it or not, and course correct on week 5.

Assuming that your quotas are set correctly (which they usually aren’t), you should expect a sales rep to hit their first monthly quota at {Average Sales Cycle Length} + {90 days}.

So if it takes 30 days to close a deal, your sales rep should hit their first monthly quota at the end of 4 months. (see, not what you expected).

Usually, if you give them pipeline within the first 3 weeks of starting the job (which I highly recommend), then they can hit time to first deal in 1 sales cycle + 30-45 days. Sometimes sooner, sometimes later, but this is a general ballpark.

So now you have two milestones a rep can work towards:

1. Time to first deal in 1 sales cycle + 30-45 days

2. Time to first monthly quota in 1 sales cycle + 90 days

What you do next, is layer out week by week what they need to do + learn in order to stay on track towards those milestones.

So example onboarding program could be:

• Week 1: Learn about the market and customer. Friday, upload a teach back video on what you learned for review

• Week 2: Learn product + how to run an intro call. End of week 2 start accepting pipeline

• Week 3: Practice intro calls, kickoff scripts, and start learning the demo. Friday upload a teach back video on your demo, get demo certified.

• Week 4: Most days are starting to get filled with intro calls, with demos and follow-up calls starting to show up on schedule. Continue practice.

• Week 5-6: Starting to work towards the first close. Learn quoting/proposal process (always drip feed the next relevant part of the sales playbook. Don’t need to do it all at once).

• Week 7: Close first deal - celebrate loudly!!!!!!

• Week 8-15: Continue closing deals. Continue reviewing pipeline with the rep. Do call coaching and start practicing skill development in areas where the rep struggles. Work your way to first quota. Continue bringing up parts of the playbook until the rep starts becoming autonomous.

This is a simplified version - I would have every week mapped out from week 1 to first quota. For the first 3 weeks, I’d also have this broken out in days.

Where ramping a sales rep fails (Math)

Sales reps need to be on 20+ hours of sales calls per week to have enough stuff in their pipeline to come close to quota.

If you’re not in back-to-back calls every day as a founder, you’re not ready to hire a sales rep.

You also need a lead channel (or multiple channels) that are producing an increasing number of meetings every week. Not a “MQL” from a webinar, newsletter signup, etc. But actual intro calls on calendar. Don’t hire sales reps to keep up with “MQLs” that marketing is generating. Reps are there to close pipeline. Make sure they actually get pipeline. If number of intro calls per week is going up, that’s a good sign. If it’s flat or declining, your sales reps will struggle.

Let’s touch on quotas for a second. In the early days, your quotas will be low. You will likely be at 2x Quota to OTE ratio. So if the sales rep OTE is $120k (salary + commissions), it’s really hard to expect more than $240k in deals a year. It will get better over time - most SaaS companies have their quotas set to 4x-7x OTE. But it’s hard to get that math in the early days.

Whatever quota you decide, it should be achievable with effort. The way to understand what’s achievable isn’t to magically come up with a revenue number in a spreadsheet, divide it by your ACV, then have that as the quota number. You will fail, they will fail, everyone will be miserable.

The best way to come up with a quota number is to look at the number of meetings you’re getting on calendar today, project the growth rate (based on how many additional meetings you’re getting on calendar each week), and then look at win rate from intro to close. Then map out how many meetings are necessary to get something to close. And see if that fills up the capacity of a sales rep. They should be spending 75% of their time working deals, and the rest on training/improving, internal meetings/discussions, admin work.

In a 40-hour workweek, a rep can realistically handle 30 hours of deal time. That’s 120 hours of closing time a month. If on average a sales cycle takes 5 hours to run (including meetings, prep, follow-ups), then they could work about 24 deals a month. With a 20% win rate, then you can expect them to close roughly 5 deals a month. Assuming that their pipeline is maxed out, always. If you set quotas significantly higher than 5 deals a month, then you’re setting them up for failure.

Quota math is hard - I gave you one scenario, but a lot goes into these calculations.

Warning to founders

If you’ve made it this far, you’ve uncovered about 40% of what it takes to make a sales rep successful at your startup.

We didn’t even cover creating rep profiles that map to your market conditions + sales process, interview guides for figuring out the bullshitters vs the real winners, what to do after onboarding, compensation plans, replicating success across multiple reps, moving from founder-led sales to player-coach to sales manager, etc.

If going through this, you realized that you don’t have this stuff figured out, then you are WAY too early to hire a sales rep.

Because sales is one of the hardest roles to hire for. You need to figure out your sales motion in order to hire the right type of rep (imagine hiring a dev without knowing what programming language you’re using).

If you get a sales hire wrong, there’s a dual cost. Not only are you paying salary + commission, but you’re giving them deals. If they don’t know how to close these deals, then they are losing revenue for your company. So cost + lost revenue = double cost. It’s very expensive to get this wrong.

And if you don’t know why you win deals, and have nothing to teach them, then the chances of getting this wrong are insanely high.

And please do not hire a sales rep unless you have real product-market fit. That never works out.

But if you have this stuff in place, you have repeatability in your sales cycles, you know why you win, you have an increasing number of sales calls in your calendar - then you have the blueprint to make a sales rep successful.

Let me know what you think of the newsletter! Always want to cover topics that you care about.

For more practical early-stage sales tips, connect with me on LinkedIn.

If you’re looking for more hands-on help implementing your first sales process, reach out for coaching packages.