When to get out of founder-led sales

When should you be getting out of sales as a founder CEO/COO?

The real answer? Never. You’ll always be involved, even when you have a VP Sales and a full team of sellers.

Sales is a critical business function tied to your ability to grow/survive. Sales pays the bills. Sales gets you your next round of funding. Sales makes you close to the market - to the customers - and gives you clarity about what to build next like nothing else.

So you’ll never be truly out of sales.

But you won’t be able to do 100% of sales by yourself forever.

So there are signs that your business is on the path to hiring your first couple sales reps.

We’ll focus on that today.

Table of Contents

• Signs you’re ready to hire sales reps

  • You have multiple sales calls a day

  • You have a lead channel that generates sales pipel …

  • Customers are renewing

  • You know why you win

• How to move from founder-led sales to a sales team

  • Hiring your first sales rep

  • Document what good looks like

  • Train, coach, develop

• Final thoughts

Signs you’re ready to hire sales reps

As you’re closing more deals, and inching towards product-market fit, you’ll want to start thinking about hiring your first couple of sales reps. Here are things to look out for that show you’re ready to start this transition:

You have multiple sales calls a day

When your calendar as a founder is getting really busy with sales calls, and that number is growing, then you’ll find yourself either not having enough time to really run your sales cycles properly. Or you’ll be saying no to other critical parts of the business to fully dedicate your time to sales.

You want to avoid hiring a sales rep until you’re on multiple sales calls every day. When you’re approaching 3-4 sales calls a day, consistently, between new calls and next step calls, then you’re likely in a position to think about hiring.

You have a lead channel that generates sales pipeline

A lot of founders think that tracking an increasing number of leads will naturally result in deals in your pipeline.

But that’s rarely the case.

The most important metric to track that signals you’re on a growth path is a Sales Qualified Lead (SQL). Meaning a prospect actually wants to talk to you because they have the problem you solve.

Anything else is just slightly better than a cold outreach. Webinar leads, most trial leads, content signups, newsletter signups, etc. They’re all great to have, but they’re not the same as an SQL in your pipeline.

So you need a channel that’s consistently driving SQLs. And that channel needs to be growing, or have the ability for you to invest in it’s growth with an increase in results.

That channel CANNOT be referrals from friendlies or investors in your network. Your sales rep can’t tap into that. So you need a channel that generates a consistent flow of SQLs.

Most deals take 3-4 calls to close. So rough math, to keep an account executive busy with sales calls for at least half of their days, 5 days a week, you’ll need 25ish opportunities in the pipeline every month.

Customers are renewing

It’s important to have happy clients before you hire a sales rep.

You likely need at least 10-20 customers that are happy, and have gone through at least one renewal with you.

When you have this, you can interview your customers around value points. Those value points will inform your positioning, your pricing/packaging. They’ll become stories and case studies.

Sales reps need this to be successful. They don’t have the founder magic that you have. So they rely on happy customer stories instead.

Avoid hiring sales reps if your 10-20 customers bought you for different use cases. You need a level of repeatability for sales to work. A sales rep needs to find more of “what good looks like.” If every customer is using the software differently, then you don’t know what good looks like yet.

You know why you win

Once you’ve landed your first 10-20 customers, you’ll generally get a sense of why you won the deal. You’ll know what alternatives you were competing against (often this is spreadsheets).

You’ll know how to handle objections or concerns in the sales cycle.

You’ll have a basic sales process that you’ve run. Discovery questions + demo + follow-ups.

And you’ll know why someone chooses to move forward, and why they decide not to buy.

This is super important to understand so that a sales rep knows when and how they win deals.

How to move from founder-led sales to a sales team

If the above is true, then you can likely start thinking about hiring your first sales team.

Here are things to consider doing and avoiding when you’re ready.

Hiring your first sales rep

When you’re hiring your first sales rep, hire a full-cycle account executive with good performance at an unknown brand.

It’s really tempting hiring someone from big brand names. The problem is that unless they were the first AE there, they’ve had a ton of brand equity, marketing, and enablement support to be successful. Those AEs are often order takers - folks are already buying the software regardless of the AE’s involvement, so the AE makes sure they have the right paperwork. That’s very different than selling at an early stage startup that’s mostly unknown, with few referenceable customers.

Also avoid hiring from the competition. They’re likely bigger than you. So the same reasons apply here. Also, the #1 rep at the competition isn’t joining you. The bottom reps would. So you’re likely inheriting a lot of bad habits, bad processes, etc., for the illusion that “they know the market.”

When you’re hiring, make sure that they’ve closed deals. A lot of founders can’t afford expensive sales reps, so they go more junior. That’s OK, unless you’re hiring an SDR who’s stepping into a first-time sales role. If you are hiring an SDR, get them sales training/coaching, find them a mentor, and teach them how to sell your product. They’ve never closed before, so don’t expect them to know how to do it. It will be your job to invest in them.

ALSO - avoid hiring a VP sales until you have at least 3-4 successful account executives closing a reasonable amount of deals. A VP Sales is there to improve the process, find out how to scale it, then hire/grow a team. If your first sales hire is a VP Sales, then they will really be an AE+SDR for their first 12-18 months at the org. Most VP Sales aren’t willing to do this, or haven’t been in a selling seat for a very long time. You’ll pay a premium to often get lower results. And they’ll pressure you to raise money so they can go hire.

Document what good looks like

Start this now, so you have something to use to onboard and train your new sales reps.

Your sales rep needs Market Knowledge, Customer Knowledge, Product Knowledge, and Sales Knowledge.

• Market Knowledge: There needs to be context set about your market category. What are the alternatives in the market. Who are the major players. In what context do we operate in.

• Customer Knowledge: Who are your customers? Why did they buy? You need to outline the problems they had with the alternatives in the market. Outline why these problems mattered, what was the impact on their business. What happened after they solved the problem? What value did your product bring. This is critical information.

• Product Knowledge: Once you’ve covered market + customer, you can dive into product. Product knowledge from a sales perspective should be enough to demo well and answer questions, but not so much that an AE could train someone. Training is a support/CS function, not sales function. Your job is to teach them about what is sellable, what workflows solve the problems, and which parts of your product are tied to the most value.

• Sales Knowledge: This is where you break everything down into a sales process. How to do discovery, how to pitch, how to demo, how to follow-up. What stages to use in the CRM. What info to capture. How to prospect. How to work leads. What tools to use, when. This is ongoing and takes a long time.

I highly recommend you record your sales calls. Then create a library of “what good looks like.”

What I’ve found works really well with onboarding sales reps is walk them through multiple successful sales cycles, start to finish.

What are your top 5 deals, that all had the same use case that made the best client?

Document how the lead ended up in your pipeline, what messaging worked to get the lead.

Record all of the calls in the sales cycle. Document every email interaction, back and forth.

Then have your new sales reps go through those recordings in chronological order so they see exactly how the sales cycle was run.

Then ask them questions about what they understood from this.

Train, coach, develop

Once you’ve hired and onboarded your sales reps, give them unlimited support. Train them weekly on different parts of your sales process. Watch every intro/discovery call they run, and give them feedback on what they’re doing well and where they can improve.

If you’re struggling with sales skills, then invest in a sales coach to develop them.

Do workshops with them regularly. Work through deals together. Be their Solution Engineer on technical demos. Join difficult calls with them. Ask them to join your sales calls once in a while (yes, you’ll still be having them).

Show them the way. And celebrate their wins, no matter how small.

Once you hire sales people, it is your job to make them successful. If they slack, don’t do the job, constantly have excuses for why they can’t do something - then coach them up or coach them out. But if a sales rep fails and you didn’t help them succeed, that’s on you, not them.

Final thoughts

Often, founders hire sales teams too early. They almost always mishire on their first head of sales.

Good early-stage AEs are hard to find. When you find them, and they’re interested in your startup, do everything you can to make them successful. And pay them well. A good sales rep will change the trajectory of your business.

But not until you’ve figured out how to sell first. Almost no sales rep can be successful in that environment. They don’t have founder magic like you do. And they can’t change the product like you can. So your job is sell > build > sell for a while.

And once you hire your sales reps, and even your head of sales - NEVER truly step out of sales. You will lose touch with the market very fast. Always do some selling. The best founders/CEOs sell daily.

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.

P.S. Starting the waitlist for next group coaching. Ping me if interested.

P.P.S I have capacity for two 1:1 coaching clients right now. Fast-paced learning, meeting every week + review your sales call. For founders who are very serious about learning sales fast. LMK if interested.