Building Sales Teams from Scratch - Navigating Sales Hiring for Startups (+ Key Stages)

So, you’re the co-founder—or one of the first hires. And sales has been dumped in your lap. 

As a co-founder, you have a unique advantage. Customers will listen to you, not because of your superb selling but because of your position. You can make executive decisions—and that gives you clout in the market and can drive early sales.

But what happens when you’re ready to scale on sales reps? The hires won’t have that advantage. And how do you scale the sales team, anyway? Let’s talk about it.

4 Key Strategies to Successfully Hire & Onboard Salespeople for Your Startup

Sales hiring is more than a job description and an interview process. And startup sales hiring? There’s additional complexity—and even more at stake.

Here are four key strategies I’ve used to hire and onboard the right people in a startup environment.

1. Document Everything Beforehand

You need to start documenting the building blocks and infrastructure of your sales process long before you bring on new sales hires. 

Document how you generate leads. If you use Sales Navigator or another tool, record yourself on a Loom going through the process. Get super specific because the way you do it is probably unique—and has an intuition for success that new hires won’t have.

Document the initial calls you get on, the emails you send, and the level of personalization you apply. Document the conversion rates at different stages in the funnel. Document that whole mousetrap you’ve built to get someone on a call and then the process you take to close them.

Why? This first part is the least difficult to pass to somebody else. These early processes don’t involve your unique value add—namely, your title asa co-founder that provides additional closing and negotiation power, especially for a small startup.

I believe anyone can be a great salesperson. But even the best salespeople don’t have that advantage.

So, document and offload the processes that don’t involve your status as co-founder. Leverage that sales knowledge—and prepare to pass it on, one task at a time.

2. Have Them Start Making Cold Calls by Noon on Their First Day

At first, you want new hires to do something basic. Almost assistant-like. They're generating leads for you, doing initial outreach, and sending emails for you. Then, they expand their responsibilities as these leads reach different milestones in the sales process.

By noon on the first day, sales hires at Close are making cold calls to people who have started 14-day free trials. We have always done this—and we always will. 

It’s partly to check that we haven't added so much bureaucracy and fluff into joining the team that we can't get them up and running successfully by noon on the first day. Consider the small stuff—can we get them a laptop? And access to things they need access to?

I also want new hires all-in and drinking from the fire hose ASAP. They're supposed to be terrible when they get on that cold call. They’re supposed not to know what they’re doing. They are simply selling a next call with another salesperson, qualifying the trial user.

3. Bring Them Along on the Sales Process

When that next call gets scheduled, they get on it with the salesperson to shadow and learn. This works the same way if a founder brings on a new salesperson. And this is what you should do for each step in the sales process. 

Bring them along to everything. (This gets easier with the right tools—like when call coaching and recording features are built into your startup sales-focused CRM.)

Once the new hire has accompanied you multiple times through a particular step, have them take over while you shadow in the background (again, made easier with Close CRM, where you can listen, whisper, or barge on a call). 

4 Key Strategies to Successfully Hire & Onboard Salespeople for Your Startup - Bring Them Along on the Sales Process

As you evaluate, provide feedback, and train your new reps, they can prepare to take on more responsibility. 

Except for closing—hold on to that part as long as possible.

4. Close Deals Yourself (to Leverage Authority & Monitor Customers)

As you offload more and more, you reach the final step: closing. Other people will now handle everything—except closing.

Co-founders have the advantage here, as shown by their high conversion rates. You can help with last-minute objections and add power to the sales offers just by your involvement. And it’s wise to take every advantage you can get.

Also, closing deals yourself provides a check on the customers your team is acquiring. I’ve watched many salespeople chase and close poor-fit deals due to improper lead qualification or feature misalignment. You want to get your process back on track to find and qualify your ideal customers—and closing yourself helps you identify any issues.

This strategy can apply even as your sales team scales. I ran a sales floor with 40 people on it, and we did the exact same thing. 

Leverage your unique power—and get good at the close

The 4 Stages of Sales Hiring for Startups

Should you even hire salespeople? Budgets are tight, and resources are limited. Your existing retention rates are okay, product development is moving ahead, and revenue is doing—something. 

So, what do you do? Check out the four stages of sales hiring for startups—and follow along.

1. Founder-Driven Sales (Founders Only)

The first person to sell your product should be you—the founder—and your co-founders, even if you hate sales and suck at it.

Do customer development yourself and get as close to your prospects as possible. This will help you when it’s time to scale up sales hiring.

Begin with the low-hanging fruit and tap into your network of:

  • Friends and acquaintances
  • Co-workers
  • Past employers

And ask for introductions left and right. 

At this point, closing deals is not the objective. Instead, focus on early-stage sales exploration:

  • Gain insights into your market
  • Understand and listen to your customers (Pain points? Responses to your solution?)
  • Test sales strategies and tactics to drive win rates
  • Discover which metrics matter to your business

This stage is about getting your hands dirty in the startup hustle and figuring out what works in the real world. The experience will help you better evaluate new salespeople during hiring time.

2. Founder-Led Sales Team (2–3 Sales Reps)

Once you have some level of sales success via initial sales, you'll ask yourself: “How do I take this to the next level?” 

Now is the time to bring on your first sales reps. But don’t hire expensive veterans—you want them young and hungry in this phase. It’s all about adding firepower to your sales efforts and replicating the results you achieved in stage one.

At this stage, you’re looking for junior sales development representatives (SDRs) or business development representatives (BRDs) who can later grow into an account executive role.

Hire two or three salespeople at a time. This promotes friendly competition and provides a benchmark against which to compare results and iterate sales strategies.

At this stage, you still need to be deeply involved. You’re managing, leading, and motivating this team. And you are still pitching, doing outbound and inbound sales, working with your reps, and listening to feedback.

You can’t outsource this. There are too many critical decisions to be made. You need these one-on-one customer experiences, different channels, and lead generation methods. It’s not enough to monitor numbers—you need to be living them.

3. Junior Sales Leader (3–15 Sales Reps)

By this point, your sales process has matured. Results are more predictable. You’ve established an effective sales funnel. You can generate consistent growth. It’s not about exploration anymore—it’s time to focus on sales execution.

And you're ready to scale your sales hiring. 

Bring in experienced sales leadership, like a sales manager or sales director. They should:

  • Fine-tune the sales approaches you’ve developed
  • Expand on what you’ve learned
  • Grow and manage your sales team (& establish a sales hiring process)
  • Set quotas, train, and coach reps

Look for someone with experience overseeing a sales team's growth from three people to 10, 20, or 30. Because that’s the next transition you’ll make—and you don’t want to be in charge of it.

This hire should have started as a junior sales rep in a previous company, grown into a managerial or leadership role there, and already managed a team larger than yours—at a company where you want to be in one or two years.

Good sales managers will improve existing structures and optimize processes. They usually don’t excel at building something from scratch and figuring things out. But they will propel your business forward if they can build on something already there.

4. Senior Sales Leader (25+ Sales Reps)

Once you’ve surpassed 15 salespeople, the next hiring breakthrough will happen at 25+.

You'll need a senior sales leader, your VP of Sales, who can manage several sales managers/directors. Find someone with a track record of successful scaling who was VP at a company where you want to be in three years.

A VP of Sales will tackle sales strategy, expanding your sales channels and partnerships, moving your customer base upstream—and improving your unit economics. They will:

  • Build an organizational structure for your sales team
  • Develop sales hiring and training protocols
  • Reorganize your commission structure
  • Groom talent for sales management positions
  • Add new sales channels
  • Close larger deals

You'll need to offer lots of money and some equity to bring this person on board. The VP will guide your sales team on a journey that will either make or break your startup—so don’t make this decision lightly. 

Once you’ve gone through these stages, you’ll have an incredibly high-functioning sales force ready to grow your startup into your dream business.

The 5-Step Startup Sales Recruitment Process

I fundamentally believe that all the best salespeople have jobs as salespeople. They are either currently in a job or are looking for one. You want to target these people during hiring. And depending on where the market is, sometimes that’s easier said than done. 

So, consider this 5-step startup sales recruitment process to come from an average market—one where the employer has as much leverage as the employee and tech layoffs or booms aren’t running the show.

1. Tap Your Network & Contract With Industry Recruiters

You should always connect with your network. That’s obvious. Do all those things you would do trying to recruit an engineer or a co-founder, and it will yield some candidates. 

And then contract with industry-specific recruiters. Looking for software salespeople? Sign a non-exclusive contract with a software sales recruiter. Many of them are pay-for-performance, which raises direct costs but ultimately saves a ton of effort, energy, and resources. 

These specialized recruiters bring you pre-screened, pre-qualified candidates. These candidates will have had conversations with the recruiter about their willingness to leave their current position, compensation expectations, and your startup status—and are primed to speak with you.

Recruiters save everyone time by delivering ideal candidates. I’ve had great success with this approach.

2. Be Transparent About the Process & Where Things Stand 

Once you talk to the candidate, be very clear about the process and where things stand at the company. Many people, especially co-founders, paint too pretty a picture of the current state of affairs within the business. You should be optimistic but honest. 

Be transparent about the features you lack, the objections you encounter, and the competition you face. On a scale of one to 10, how hard is it to sell your product? If it’s tough, lean into that. Tell them: “It’s tough, but we’re gonna figure this out together.”

If you reveal all the weak points and warts in your business, and they still want to join? They are either (1) very, very desperate or (2) a great candidate and get excited about the journey.

Try to figure that out—but remember, you won’t hit 100 percent hiring success. Some people will join, and it will go terribly. There’s no magic 20-minute conversation that will tell you whether this will be a great fit. You will find out in 30 to 45 days. So, deal with that reality as it comes.

3. Conduct Mock Trial Calls 

At Close, we do a mock call during the interview process—and have for almost a decade. 

There’s no trickery. We tell candidates ahead of time to choose whatever software product they’d like and assume we’re qualified. Then, they take us through the demo.

What are we looking for? Communication style. Do they engage my attention throughout—or do they lose me? Are they long-winded? Do they ask questions and listen to the responses? And even more so: Did they come prepared, or just throw something together?

I’m not looking to be convinced to buy the product they’re selling. I don’t care that much about the core material. I’m looking for intangibles, culture fit, and skillset. I want to know how they handle things and what they can work through. 

I want to see what the experience is like for me—going through a demo with them.

Pro tip: We have an additional exercise for sales hires at Close. Our company is fully remote, so most of our internal communication is written and asynchronous. So, we ask candidates to create a sales sequence. We want to see their thought process, and how effectively they can communicate in a written format.

4. Hire in Pairs

If you can manage it financially, hire in pairs. Startup sales is difficult—and it's great to have someone to commiserate with who is on the same journey. Plus, you become less dependent on individual sales performance. 

More importantly, two samples provide a performance benchmark against which to measure. 

Comparing your sales performance with your sales reps is a terrible benchmark. Why? You have advantages that reps don’t have, based on your title and that perception in the market—which has nothing to do with your ability. So, by hiring two salespeople, you create a reasonable, accurate foundation for comparison.

And don’t make it a “kill one another, last person standing wins” situation. If you go two for two, great! Set minimum expectations when they start—and see what happens.

5. Keep Compensation Stupid Simple

I’m not a fan of wildly optimistic and unproven compensation structures. Pay your salespeople a base. That base should be enough to cover rent, feed their children—and whatever else, so they can come to work and not have to worry about basic necessities.

Startup sales is inherently volatile. Your product will pivot, and so will your sales approaches. You need that flexibility early on. So, it’s only fair that your team is compensated accordingly with a high percentage in the base, having set clear performance expectations.

The other part of their compensation—about 20 percent—should be the optimistic part. 

Set above-and-beyond expectations and reassess those standards quarterly. Why? Your activity and results will be far different in six months than they are now. 

At Close, we’ve had the same basic comp structure for our account executives for three years. We’re a mature business, and a lot of our mechanics are predictable. But still, it resets quarterly. 

We discuss any macro environment changes, and how hard sales will be this quarter, based on product or pricing changes, marketing efforts, or lead gen assistance. We talk about it, get feedback, and iterate the compensation structure.

So, the base covers what you expect them to do, and the additional covers what they accomplish beyond that. And you reassess it quarterly.

Pro tip: Keep in mind that the base will be higher if that full-time employee lives somewhere like Chicago, San Francisco, Los Angeles, or New York. Filter out candidates, if necessary.

Pursue the Right Sales Hires to Boost Startup Business Development

Startup sales is tough. And hiring for startup sales can seem like a minefield of missed opportunities and resource drains.

Startup jobs—whether in SaaS, healthcare, or something else—aren’t exactly renowned for their stability and stellar compensation. To attract and retain the right talent, you need to have the right approach. 

Get your documentation and mindset in order, follow through the stages of startup sales hiring, and develop a recruitment process that secures the right people—the ones excited for the journey and hungry to see your sales soar.

As your tech startup pursues business development and related sales goals, the right sales team can make all the difference.

Want more details? Grab our free resource: The Sales Hiring Playbook.