How to Build a Sales Team: Your First Hires, and in What Order

You thought you'd hired reps who could close. That's how the CEOs who call me start. Deals still close when you're on the call and stall when you're not, and the last sales hire cost you six months and no sales. So you searched how to build a sales team, and found org charts.

Most guides start there: SDRs feeding account executives, account managers behind them, a manager over each. Under $15M, with one to five reps and you still closing, the org chart isn't the question. Who you hire next is, and what has to be true before you do.

The order you hire in matters more than the structure. Every hire made before the one it depends on comes back to you. Below is the order I'd hire in, what each hire costs in this market, how to hire a salesperson without getting burned again, and the hire that comes too early.

I've had a quota on me for 27 years and never missed, most of it in leadership. I've built or rebuilt the sales organization at every company that's employed me.

What Building a Sales Team Means at a Company Under $15M

Building a sales team is deciding who prospects, who closes, who manages the accounts and who manages the people, and which sales roles carry a quota, then hiring and training those people in order. I'd define it by what each role has to inherit from the one before it.

Sales Team Structure: The Three Models, and the One You're Running

Three sales team structures come up in most of what you'll read. In the island model each sales rep runs the entire sales process, from lead generation through the purchase to the renewal. In the assembly line each stage of the buyer journey gets its own role: SDRs set meetings, account executives close them, account managers keep the existing customers. A pod is one of each around a market, so the customers see one team.

With one to five reps, you're running the island model whether you chose it or not, with one difference: the island is you. The CEOs who call me describe it the same way: their reps set the meetings, and they close them.

The assembly line comes once there's enough new sales to split the work. Split it before then and you've added salaries to the island, and the island is still you.

Why the Order Matters More Than the Structure

All three structures assume someone already runs sales: a manager coaching the reps, sales leaders above them, an owner for every stage. Under $15M, that's usually the hire nobody has made yet, and the reps report to the CEO who's also closing their deals. A structure says who owns each stage. The order says who gets hired while nobody owns any of them yet, and that's the decision below.

Why Your First Sales Hires Didn't Work

CEOs describe their first sales hires to me in the same words, and the first four signs below are theirs. The last one is mine.

• The VP of sales from the bigger company. They brought the playbook from their last company, and it didn't fit how your business sells. Founders tell me the whole team slid back to what it was doing before.
• The rep with the rolodex. Great interview, great contact list, great meetings with big names. No closed deals. Founders say it took them a year to see it, because the meetings never stopped coming.
• Commission only. It felt safe because it cost nothing until a deal closed. Nothing closed, and it cost the time.
• Zero onboarding. The rep started on a Monday with a laptop, a login and your calendar invites, and learned by watching you. Founders tell me that's when they got pulled back into sales.
• The hire was made before the process existed. That's the one I find behind the other four. The rep wasn't the mistake. The timing was: they were hired into a role nobody had written down, so they sold the only way they knew.

In those companies, the reps could only copy what they saw on the founder's calls, and the founder rarely ran two calls the same way. If that's the company you're hiring into, the next rep has the same calls to copy, whoever it is. The process comes first. Founder-led sales →

The Order I'd Hire In

The order I'd hire in at a company under $15M: a sales process and someone who owns it, then a first rep who can close, then a second, then outbound, then a sales manager, then a VP of sales once the process works. That's the sales team structure, in the order it gets built.

Whoever runs sales owns each of these hires: writes the job, runs the interviews, owns the first ninety days. You make the final call. Here's what has to be true before each one.

Before anyone: a sales process, and someone who owns it. Who you sell to (the ideal customer profile your best customers fit), what you say, how a lead gets qualified, how a deal moves and what has to be true before it moves. Built into the CRM, so the tools carry it and the data is there to read.

It can be you, if you have the hours. If it isn't, the person who builds it is your first hire, before any rep, and who that should be is under who should build your sales team, below.

Hire 1: a rep who can close. One salesperson who takes the deals you hand them and closes some without you on the call. Not an SDR, and not a VP yet. That's the first proof you have a sales process and not a founder. Give them your pipeline, not a cold list, so the first ninety days test their closing and not your lead generation.

Hire 2: a second rep. Two reps give you something one can't: a comparison. If one closes and one doesn't, you learn whether the problem is the rep or the process. One rep leaving also doesn't zero the team. I'd add the second once the first rep has closed deals without you, not before.

Hire 3: outbound. An SDR, or a rep whose job is new pipeline, once your reps close what they're given and the limit on growth is how many deals come in. Marketing is supposed to deliver leads and sales is supposed to find its own, so decide which of the two this role answers to first.

Decide it after, and the SDR's meetings land on the one calendar that's always open: yours.

Hire 4: a sales manager. When every deal needs inspecting every week and you can't, someone has to. Somewhere past three reps, and never before the process exists: a manager hired before it has nothing to manage.

The role is sales coaching and ongoing training, the weekly one-on-ones and performance reviews, the pipeline review and the forecast call, with no accounts of their own. A manager who carries deals and forecasts them with nobody looking is grading their own paper.

This is where your best rep comes up. Every great rep doesn't make a great leader, and every great leader isn't always your best rep. Promoting your top closer costs you the top closer, and if the promotion is a reward, the team gets a manager who'd rather be selling.

Ask them whether they want to coach the other reps' deals instead of closing their own. If the answer is a pause, you have your answer.

Hire 5: a VP of sales. Once the sales process works and someone has to run and grow it for years. Hired before that, a VP of sales has nothing to run, so they build what they ran last. What that experiment costs is in the cost section below.

The hire that comes when it comes: account management. The moment renewals and existing customers are pulling your reps off new business, split the job. Account managers are a different job from closers, with a different focus, and they're paid differently. I wouldn't ask one person to do both for long.

How to Hire a Salesperson Without Getting Burned Again

This is the hiring process I'd have whoever runs sales run for a rep at your size, with you signing off on the hire. Each step closes one of the five ways the last hire went wrong.

1. Write the job description from the deals. List the last ten deals you closed: who bought, what they were trying to fix, how long the sales cycle ran and what nearly killed it. The job description and the skills profile come from that list. I'd rather hire against ten real deals than a template. The template hires the rep who interviews well; your deals hire the rep who can close yours.
2. Match the sale they made to the one you make. Say one candidate sold a $500 subscription in a week and another sold $200,000 of services over nine months. Those are different jobs. Ask for the deal size, the sales cycle length and who signed on their last three deals, and match them to your customers and your sales cycle.
3. Interview for closing, not for the rolodex. A contact list is a list of people who bought something else from someone else. The test I'd use: give the candidate one of your real deals and a page of notes, and have them run the next call with you as the buyer. In twenty minutes you'll hear whether they ask the question that matters or pitch.
4. Ask about the deal they lost. The one they were sure of that didn't close. A rep who can tell you what the buyer did instead of what the buyer said is one you can forecast with.
5. Pay for the job. Not commission only; CEOs tell me they tried that. The 70/30 rule, 70% base and 30% variable at target, fits when marketing hands the rep the deal, and the rest of the plan is its own page: Sales comp plan →
6. Plan the first ninety days before the offer. A 30-60-90-day plan is what a new rep does in each of their first three months: thirty days to get a clear sense of the product, the customers and the objections; sixty running calls with someone in the room, which is you until someone else runs sales; ninety carrying deals alone. In my experience, the reps who get that onboarding and training are the ones who stay.

How Much Does It Cost to Hire a Salesperson?

In this market, a quota-carrying rep at a company under $15M costs the business their on-target earnings plus the months before they produce.

Say you set OTE at $180,000 from what the market pays the job, at 50/50: $90,000 base and $90,000 variable at a $900,000 quota. Add payroll taxes and benefits, a recruiter's fee if you use one, and three to six months of ramp, which is three to six months you're still the closer.

Founders count the failed hire in months. A rep who produces no revenue for six months cost you six months of doing the selling yourself while paying someone else to do it, and two of those is a year.

A full-time VP of sales, in this market, at a company under $15M: $360,000 to $520,000 a year fully loaded, plus equity, after a search of three to six months. Hire one before the process works and that's the price of the experiment. The comparison is its own page: Fractional vs. Full-Time →

Scaling a Sales Team Without Becoming the Bottleneck

Scaling a sales team means adding reps who close without you, so revenue grows faster than your calendar. Adding reps to a team that closes only with you in the room scales the thing you were trying to get out of.

The sign I look for: count the deals closed without you on the call. If that number is flat after two new reps, the sales process isn't there yet, and the third rep doesn't fix it. The reps sell the way they did before, sales performance stays where it was, and you're back in the deals.

Then there's the manager, Hire 4 above. Someone reads the CRM data on every deal every week: what did the buyer do last, what did they agree to next, when. Until that someone exists, it's you, and you've scaled the team into a second full-time job for yourself.

The manager hire is the one that lets you read the forecast on a Monday without being in the meeting. Some deals will need you while the team learns, and I'd expect that count to shrink. The deals that still need you have their own page: Sales forecasting →

Who Should Build Your Sales Team

In my experience, under $15M there's rarely a recruiting team or a sales operations team for this. The hiring, and the sales team structure it builds, falls to whoever runs sales, with you making the final call. It's the decision the CEOs who call me made their last hire without. The ways to fill the role:

You. It's right if you have the hours to write the process, run the interviews and train and coach the first rep through ninety days. Most CEOs who call me don't.

A rep you promote. Right when the sales process works and someone on your team already coaches the others and wants the job. Hand them the hiring too early and they hire reps who sell the way they do.

A sales recruiter. A recruiter finds sales talent, and the fee is earned the day one is hired, whether or not they ever close. What they can't tell you is whether your sales process is ready for the person they found, so use one once the job is written.

A sales consulting firm. Fits when the process needs building and someone inside will run the hiring once it's handed back. In this market, a typical engagement is a 90-day sprint: the audit, the playbook and a CRM rebuild, handed back to the team that made the last hire. Nobody from the firm stays to lead it. The complete guide to sales strategy consulting →

A full-time VP of sales. Worth it when the sales process already works, so the person you bring in builds the team on it instead of inventing it, and when you need someone in the building every day, committed for years.

In this market, at a company under $15M, that's $360,000 to $520,000 a year fully loaded, plus equity, after a search of three to six months.

A fractional VP of sales. The route when nobody inside can run sales and you're still the one closing. A fractional VP of sales is a sales executive you bring in instead of hiring full-time. In this market, most are sold by the hours a week at $4,000 to $15,000 a month, often through a network that assigns the consultant, so you don't choose who shows up.

Done my way, the hiring is mine: I write the rep job descriptions from your deals, run the interviews, and you make the final call on every hire. Then I run their first ninety days, coaching on live deals, with a development plan for each rep and the hard conversation when one is needed, with you told first.

I'm rarely the first fix a CEO has tried. Usually it's been one train wreck after another. This time it's one person: me, with no associates and no bench. Your sales team reports to me, I report to you, and your head of marketing stays my peer.

The new revenue the team closes is my number, and I take no accounts of my own, so deals don't start waiting on me instead of you. When the number misses, you hear it from me first, with the reason and what changes next month.

Since 2020, averaged across my fractional clients: three times as many leads turning into opportunities, and two to six times the pipeline.

From month one it's aimed at one of two endings: someone on your team grows into leading sales, or you hire a full-time VP of sales into a process that already works. When it's time, I write the job description with you and sit in on the interviews, so they're hired against the real job.

Mine is $5,000 to $7,000 a month, remote, month to month, with no minimum term and no notice period: if it isn't working, you stop at the end of the month. That starts below the market's $6,000 to $10,000 middle, and your number is mine, no excuses: Fractional VP of Sales →

Advisory. If someone on your team can run the hiring once they know what to hire for, you need advice, not a leader. In Advisory, I tell you who to hire, in what order and why, and your team runs the hiring; nothing reports to me, and I answer to you. It's $3,000 to $4,000 a month, remote: Advisory →

How to Tell the Team Is Working

A sales team is working when deals close without you and each hire is doing the job it was hired for. Read these every month with whoever runs sales, in this order:

• Deals closed without you on the call. The number that tells you whether you hired salespeople who can close.
• New pipeline by who created it. Whether the outbound hire is bringing in deals the reps can close, or meetings nobody can.
• Time to first deal for each new rep. Against the ninety-day plan. A rep with no closed deal at day 120 is a conversation, not a wait.
• Conversion rates by stage, by rep. The comparison two reps give you. If one converts at proposal and one doesn't, you know where to coach.
• Quota attainment. About two-thirds of the team reaching it is the common standard. All of them and the quota is low; none of them and it's the process.
• Your week. How much of it still goes to sales calls, and how much to the customers and clients who need the CEO.

Sales teams don't improve overnight, so give each new team member the full ninety days before you judge success against these.

When Should You Hire a VP of Sales?

When the sales process works without you, two or more reps close on it, and someone has to run and grow it for years. Between now and then, someone has to run sales well enough that the VP inherits a job instead of inventing one. That decision is who should build your sales team, above.

The first quarter your reps close without you, start writing the VP of sales job description from what the job turned out to be, and hire them against it. The leader is the last hire, into a team that already works.