Every founder needs to understand how to build a sales team. And in all honesty, it’s not easy. Let’s start with the concept of you don’t know what you don’t know yet. And the sooner you recognize this, the faster you can reach revenue targets. There’s a right way and a wrong way to build your sales team, especially when moving from founder led sales into your first hire(s). Unfortunately most founders build their sales team backwards.
- They hire a VP of Sales before they’ve closed enough deals themselves.
- Then they hire a VP of Sales with a strong pedigree and logo history, not one who’s actually built something.
- They hand over the pitch deck, a CRM login, and expect them to start closing immediately.
There are actually a ton more sins that founders make, but we will just start here for now.
What You’ll Learn About How To Build a Sales Team
- The order to make your first four sales hires.
- Why you never hire a VP of Sales first.
- When is the right time to start scaling your sales team.
- When to hire the player/coach.
- What you need and don’t need before you hire anyone.
- How important industry knowledge is in sales hiring.
- How to avoid the two most expensive sales hiring mistakes founders make.
Start With You, Not a Job Posting
If you haven’t closed between 15-20 deals yourself, it’s too soon for you to hire anyone including SDRs, AEs, Managers, or a VP of Sales. Additionally, at least half the deals you’ve closed need to come from someone other than your VC and people you know. You need to have closed real deals, and yes, you need to have lost some too. And you need to document the deals you’ve closed. I don’t mean in a CRM, I simply mean get all the information out of your head and onto ‘paper’ so it can be taught and learned. It doesn’t need to be perfect and it will improve over time. Still, you must have this information outside your brain.
If you skip this part, essentially, you’re hiring someone to solve a problem you don’t understand yet. And you are basically hiring someone to do market research for you, not sell.
You think you want to write a job description and hire a ‘closer’. In reality you need someone who understands how to navigate prospects and customers with an unstable product/market fit. What you really need is someone who can sit with ambiguity, lack of resources, data, customer feedback, and be comfortable figuring it out.
If you rush through founder-led sales, it’s like rushing the build of parts for a car without first testing them. You’d never write code, or even trust AI to build the code, without testing it some before release, right? Founder-led sales is simply a different R&D phase of your go-to-market motion. Treat it like one.
Hire In This Order (Not All at Once)
Founders love to hire a “sales team” like it’s one purchase. It’s not. Each hire should answer a specific gap, in this order.
1. Your First Two Reps Should Be Generalists, Not Specialists
Let’s pause here for a moment. Yes, you always hire in pairs. If you only hire one at a time and they fail, well, you’re going to fall behind, and in today’s market, you won’t be able to catch back up. And don’t worry about salary. You are not committing to two one-year salaries, you’re committing to 6 months of a single salary. If in 90 days one of them does not work out, you make the necessary changes and you aren’t having to start over. If they both work out, then the revenue growth will reduce your cash flow concerns around hiring two people. Either way, you win.
Your first sales hires need to have experience doing everything: prospecting, qualifying and discovery, demo, negotiate, close, and hand off to onboarding. You’re better off hiring people earlier in their career and hungry than someone with a logo. Nobody outside of you cares about that logo. Your prospects won’t even know. Don’t hire a pure hunter or a pure closer yet. You don’t have the volume to specialize in roles.
If you can find someone who has been the ‘first sales’ hire before and is willing to do it again, that’s generally your best bet. Enterprise reps who’ve only ever worked inside a mature sales org with a marketing engine feeding them leads will struggle here. There’s no engine yet. They are the engine.
2. Your Next Hire Fills the Gap Your First One(s) Exposed
Once they start to close consistently, you’ll see where the machine breaks. Maybe pipeline generation is the bottleneck, maybe onboarding is the issue. Simply hire for the gap you can see, not the org chart you imagine.
And remember, you’re not done with sales yet. You still have to be a part of the conversations. If you’re just passing it off and think the deals will close, you’re making a grave error. Additionally, you need to continue documenting what good and bad look and sound like. Whether it’s the pitch, the deck, handling objections, whatever it is, document it. Our guide on creating a repeatable, scalable sales process walks through exactly how to turn what’s in your head into something a new hire can actually follow.
3. Your Third/Fourth Hires Should Prove the Process, Not Just Throw Bodies at Revenue
By now you’re testing whether your process works for someone who isn’t you and wasn’t your first hire. Onboarding for your next rep should take half the time it took your first rep. If rep three flounders in a similar way to the first rep, then you don’t have a strong sales onboarding process, you just got a lucky first hire.
This is the stage where a lot of founders panic-hire a sales manager. Don’t, yet. You need proof the model repeats before you need someone to manage it. Yes, this will stretch you thin, and that’s part of the learning about leading sales. You have to experience this if you want to truly understand and grow revenue.
4. Your First Sales Manager Comes After the Model Repeats, Not Before
Note, you’re still not hiring a VP of Sales yet. You don’t need one. You need someone who can coach your sales team, review and audit the process, and help drive revenue. And the best practice is to promote someone from within. Reward the early reps who came in and helped figure this out. This doesn’t mean promoting the rep with the best closing, it means promoting the rep that understands how to manage and navigate people and processes.
A sales manager’s job is to coach reps against a known standard. If there’s no known standard, there’s nothing to coach against, and you’ll end up with a manager who’s simply creating and staring at dashboards thinking they are a sales leader. Wait until you have 3-4 sales people with a repeatable process before you hire that sales manager.
5. When to Hire a Player/Coach Sales Leader
This is easy: never. This never works out well for them or you. Just because you don’t want to commit the extra salary does not mean someone can actually do both jobs well. Yes, they could do some, but it will never be enough, and it hurts you in the short and long term.
What to Build Before You Hire Anyone
It’s simple, you need some level of documentation as previously discussed. New sales reps don’t ramp slowly because they’re bad at sales. They ramp slowly because nobody wrote anything down.
Before your second hire starts, you should have:
- A one-page description of your ideal customer, in plain language, not a persona slide.
- The top 3 use cases of the pains you solve, not what you do, as they relate to each persona.
- The top five objections and how your best rep (probably you) actually handles them, not a canned script that creates confrontation.
- A rough map of your sales stages and exit criteria. Here’s our recommendation. Note, ‘Demo’ is not a sales stage, it’s an activity.
- A list of the deals you’ve lost and why, reviewed honestly, not spun.
None of this needs to be polished. It needs to exist. A messy document beats a perfect memory that only lives in the founder’s head. And no, you don’t necessarily need a CRM between your first and second hire.
Hiring Criteria That Actually Predict Success
Don’t get seduced by the hype on a resume. Resumes lie, learn to inspect professionally. What they did in the past is not always an indicator of what they will do in the future. What predicts success is watching someone actually sell, under real conditions, before you make an offer.
Ask candidates to walk you through a deal they lost, in detail. Not the highlight reel, the loss. How they handled it tells you more about their grit and self-awareness than any “tell me about a time you overcame a challenge” answer ever will.
We go deeper on the specific traits and interview techniques that separate a real closer from someone who just interviews well in our piece on how to hire killer sales reps. Worth reading before you write your first job post.
The Two Mistakes That Cost Founders the Most Time
Mistake one: hiring a pedigree before you have a system. An expensive VP of Sales dropped into a company with no process, no documented ICP, and no proof of repeatability will spend their first year building the exact same things you could have built for a fraction of the cost. As my friend Scott Leese says, “Hire for ‘can do’, not ‘has done’.”
Mistake two: throwing bodies at the problem. Hiring a full team at once because the round just closed is a vast waste of time, energy and resources. Five reps hired the same month means five people ramping on a broken process simultaneously, with nobody who’s actually proven it works yet. You’ll burn so much cash and have nothing to show for it.
Coaching Your New Team Once It Exists
Early stage hiring is often a bit easier, and sometimes more fun. That’s because everything is new, everyone is working to figure it out, and you’re all in the boat together. Keeping a sales team performing after the new-hire energy wears off is where most founders struggle the most. You need a sales coaching rhythm, not a weekly pipeline review.
Our sales coaching guide for sales leaders breaks down what actual coaching looks like versus the fake deal-review theater trap most sales managers fall into. Your job is to make the team better, not bigger.
FAQ
When should a founder make their first sales hire?
Do not hire any sales personnel until you have personally closed 10 to 20 deals yourself. And those deals cannot just be friends and family. Hiring before that point means you’re paying someone to do market research, not sell.
Should my first sales hire be a VP of Sales?
Absolutely not. You will waste time, money, and energy. Your first sales hire should be a generalist who can prospect, demo, negotiate, and close without a built-out team supporting them. A VP of Sales needs a system and a team to lead. You won’t have either yet.
How many sales reps do I need before I hire a sales manager?
Most founders hire way too soon for a sales manager because they want to “get sales off their plate.” Best practice is generally to hire a sales manager between the 3 and 4 rep mark, and in reality, it’s often someone who’s promoted from within. This is the advantage of being an early sales hire at an early stage company. Hiring a manager before the process repeats just gives you an expensive individual contributor with a manager title.
What’s the biggest mistake founders make when building a sales team?
To be honest there is way more than one mistake, we know of and discuss at least 30 sins and mistakes founders make. Often the biggest one is hiring for headcount instead of hiring for the specific gap in the machine. A close second is hiring senior, expensive talent before there’s a documented process for them to run.
How long should it take a new sales rep to ramp up?
This is actually a trick question. Everyone thinks it’s based on a timeline because you’re in a hurry to reach revenue. And yes, you are, that doesn’t mean you can put a timeline on it at the founder-led sales transition stage.
If you’ve documented your ICP, objections, and sales stages before they start, a competent rep should be contributing pipeline within 30 days and closing within 60 to 90, unless it’s a true enterprise sale. If the ramp is taking longer than that consistently, the problem is usually the process, not the person.
Do I need a sales playbook before I hire my first rep?
You need more than an outline, but you don’t need something polished and perfumed. The basics should include your ICP, objections, and stage definitions, exit criteria, competitor matrix, and pricing. What matters is that it exists somewhere other than your own head before you ask someone else to execute it.
Does industry experience matter when hiring a sales person or building your sales team?
Most people love to say this matters, and unless you are selling something very scientifically specific, industry experience does not matter in sales. What matters is sales experience, not industry experience. If you can find someone who has been successful at sales, understands what it means to be a first time sales rep at a start up. That is worth more than any industry experienced sales person you can find. You can learn the industery pretty quickly, especially these days. You cannot simply read a book about sales over the weekend and become an expert.
Ready to Build This the Right Way?
Whether you’re a founder or sales leader struggling to figure this out, this is where we can help you. More than happy to talk about it. Book a call and we can discuss your challenges and goals, and make sure you’re not making the mistakes others have made.
