Ask just about any founder what the hardest part is about building from 0-1, and assembling the early team will likely come up near the top of the list. When the rules of the game you’re playing and the winning strategy can change on a dime, finding skilled, adaptable players (who are also willing to join your underdog squad) is incredibly tough.
And from what I’ve seen, the batting average for making a successful first sales or revenue hire is especially low. Sub-one-year tenures are ridiculously common — frankly, that’s pretty bleak.
For a startup still in the early levels of product-market fit, a revolving door of sales leaders can leave the entire team feeling dizzy. A bad hire doesn’t just cost you the money (and time) it took to train them. It’s all the botched deals and prospects that walked out the proverbial door, and into the hands of your competitor.
So why, despite it being so critical to get right, do these early sales hires have a tendency to flame out?
I have my own theories on sales leader stickiness, based on what I’ve seen play out as an investor advising founders navigating this tricky hire, as well as a former GTM leader on the other side of the table. In my view, two mistakes crop up most frequently.
The first is missing the mark on the level — usually overshooting the seniority that your startup actually needs. If you have a chance to hire a former VP of Sales at a big-time company, or someone with 20 years of experience in your industry, that’s an exciting fish to reel in. But here’s where things tend to go wrong: When it comes time to actually do cold outreach and build a sales process mostly from scratch (which is what you need in the early days), these folks are often many layers removed from the true blocking and tackling work of startup sales. In the words of Dock founder Alex Kracov, you need to hire someone who is comfortable with doing their own button-clicking.
The second mistake I see is founders jumping the gun altogether on this hire. As we discussed at length in our last installment in this series, sales is normally unfamiliar (and awkward) territory for founders. So after founders assemble those first few deals, there’s a strong urge to hot-potato sales to more capable hands.
But I've seen this premature hand-off lead to fumbles. Making your first dedicated sales hire too early can be just as damaging as waiting too long — and in my experience, the former is far more common.
Before hiring your first salesperson, you don’t need to have the exact recipe made yet. But you should have most of the ingredients in the cupboard.
-Meka Asonye, Partner at First Round Capital
The result, as Mike Molinet (who scaled Branch to $100M and is now on his second startup Thena) put it to me, is like a science experiment gone wrong. “Any scientist will tell you that you don’t want to test multiple variables at once. But when you make a sales hire too early, you’re now evaluating, 1) whether that person is successful. 2) Whether you have a repeatable sales process. And 3) whether the product is even aligned to solve the right problem,” he says.
These are the types of chaotic conditions that can make sales an easy scapegoat — and founders mistake a people problem for what is, in fact, a process or a product problem.
In trying to source helpful resources for the founders I partner with, I’ve found there’s surprisingly little concrete guidance available on this critical inflection point. When exactly is the right time to bring on your first sales hire? What profile should you look for? How do you set them up for success? The standard playbooks often fall short because they're written for later-stage companies that have already figured out their sales motion.
To help answer these questions, in addition to speaking at length with Molinet, I also sat down with an epic group of early sales hires. It is not easy being a “first” anything when it comes to startups, and these folks have plenty of expertise to share for founders looking to find their just-right hire and avoid the dreaded organ rejection.
Some of the folks you’ll recognize from our previous installment on founder-led selling, as well as a few new faces who generously opened up their playbooks:
- Becca Lindquist, who is the VP of the Americas org at dbt Labs, and was the second sales hire at Heap when the company was sub-$1M in revenue.
- Michael Loiacono has been one of the first 20 startup employees 6 times in his career, and is currently the VP of Global Sales at Testlio.
- Jacquelyn Goldberg, who was the first sales hires (and the 6th employee) at PebblePost and then went back to the 0-1 sales trenches as the former VP of Global Revenue at Sama
- Sam Taylor, who as Dropbox's first enterprise sales rep helped the company crack the code on moving upmarket before going on to lead sales at Quip and help build Loom's revenue engine.
- Eric Lasker, who started as one of the first sales hires at Stripe — back when there was no brand and no playbook — and is now leading the commercial charge at Varda Space as CRO
- Kyle Parrish, who was the very first sales hire at Figma when the company was at $2M in ARR (and recently wrapped up an incredible 6-year run)
While these folks have been a part of building and selling vastly different products, through these conversations some clear patterns emerged about what works when you’re making your first sales hire and how to avoid the revenue leader conveyor belt. Let’s dive in.
When is the right time to hire? Focus on signals, not timelines
Before we dive into finding your just-right sales hire, let’s first unpack getting the timing right. Because being off a few ticks here, and you’re nearly guaranteeing a poor match — even with an exceptional candidate.
As dbt’s Becca Lindquist told me bluntly: "If you bring in a sales hire too early, you're expecting them to come in and work wonders when you haven't shown that you have a product that people actually want to buy. Do you have enough traction and validation to support a rep? Otherwise, you're setting them up for failure."
Here are a few signals that your startup has enough wind in its sails for full-time sales (last time I’ll make that pun, I promise).
Signal 1: You have at least a dozen customers (who aren’t your besties)
So when is it not too early? The consensus from the folks I talked to is the same: Don’t hire until you’ve crossed the threshold where you’re confident that 1) there’s a market for your product and 2) your product is actually solving the problem you’ve identified. Usually, this is in the neighborhood of at least 10, but probably closer to 25 customers for B2B companies. Becca Lindquist adds an important caveat here: “Having 10 customers who are all your best friends doesn’t count.” (When he was building Sprig, for example, Ryan Glasgow even went so far as to completely avoid selling to people he remotely knew.)
Once you cross that dozen-ish threshold, the question of when to hire I’ve found is more of a spectrum than a binary answer — it could fall anywhere between “after validating that the earliest signs of PMF exist” and “can successfully and repeatably sell via cold outreach.” Enterprise products may need fewer logos, PLG products may need more. And complex sales motions might be even harder to disentangle yourself from. For example, EvolutionIQ, which sells AI-native software for insurance companies, didn’t sign a single deal without founder involvement until 2024, five years after starting the company.
If you hire a salesperson really early, like in the first five customers, I’m not confident that you’ve actually validated the problem and your buyer deeply enough.
-Becca Lindquist, VP Americas at dbt Labs
Signal 2: You have a repeatable (if not perfect) sales process
Far too often, I see founders who have powered their way through founder-led sales, by sheer force of will, and then hope that a first sales hire will come in and clean up their messy, unstructured process.
And while I don’t think you need some ultra-sophisticated sales motion, complete with airtight first call decks and a mature CRM, there should be some degree of repeatability — not a collection of one-off wins.
Mike Molinet made this mistake while building Branch as a first-time founder. “When we first started to monetize, I went out and hired a VP of Sales and gave them 100 things to figure out. But there’s no way a sales hire can be successful while figuring out the CRM, the ICP, the persona, building the team and figuring out sales development. When you’re ready to hire, give them a narrower scope.”
If you can’t clearly articulate how your last five deals got done, you’re not ready for a sales hire.
-Mike Molinet, co-founder of Thena and Branch
So before hiring your first rep, you should be able to answer these key questions from your own founder-led selling experience:
- Who is your ideal customer profile (ICP)?
- What is your typical sales cycle length?
- What are the common objections and how do you handle them?
As you’re moving through the founder-led sales phase (and well before you bring on a dedicated hire), make sure you’re filling up your notebook. When my partner Brett Berson got a chance to sit down with Figma’s very first sales hire, Kyle Parrish, that was exactly his advice.
“Founders should have some notes — they don’t have to be perfect — on how to do high-quality discovery and convert customers. From there, it’s the sales leader’s job to build on what the founder has learned,” he said.
But, admittedly, this was far from his experience in the early days of Figma, at around ~40 employees and $2M ARR. “There was no documentation. I couldn’t come in and read the notes on working with Microsoft and what that relationship looked like, for example. It was very challenging to have limited information on what was happening in the field.”
Signal 3: You’re dropping balls
One of the clearest signals that it's time to hire is when promising opportunities slip through the cracks. “It’s a bandwidth issue. At the end of the day, do you feel like there’s opportunity falling on the floor?” asks Sam Taylor.
Do you have deals where you realize, “Oh shit, we have people who are our perfect ICP who we haven’t talked to in 3 months?”
-Sam Taylor, former VP of Revenue at Loom
Jacquelyn Goldberg (former first sales hire at PebblePost) agrees here — if you don’t feel that you’re spinning plates and glass is shattering around you, chances are you’re not ready for a full-time hire. “There’s a cash crunch that startups are always up against. But now you’re paying a salesperson for a really long runway before they can start returning value,” she told me.
Signal 4: You have a “minimum viable business unit”
Far too often founders oversimplify here. Hire a seller, be rewarded with a more robust pipeline and closed deals. But the wheels need a bit of grease.
“There are a lot of things in the bucket of generating pipeline. Do you have money for the sales hire to put on an event? How closely involved is the founder with executive relationships in your top accounts? Do you have post-sales support (even if it’s just someone on the team who wears this hat part-time)?” Becca Lindquist told me. “I’ve showed up as a first sales hire where they didn’t even have my phone set up and the minimum business unit was me. That was a big red flag. Versus at dbt labs, they had a really robust open source community that we could use to build traction and expand.”
Who should you hire? Avoid the Rolodex Trap
The conventional wisdom pushes founders toward hiring experienced reps with flashy brand recognition. After all, if someone was successful selling at Salesforce or Snowflake, surely they can help you build your sales motion from scratch, right? But from what I’ve seen, the safe choice is very seldom the right one.
“It’s the most common mistake, and it’s one I made multiple times at Branch,” Mike Molinet frankly told me.
Hiring late-stage, coin-operated people almost never works for early stage. They’re used to having an army of support teams and systems behind them — legal, security, product market, revops.
-Mike Molinet, co-founder of Branch and Thena
Becca Lindquist gives this a strong plus-one. “They’re coming in with all sorts of preconceived notions and often forget that they also have to go and generate a lot of their own pipeline,” she says. “Hiring the enterprise rep who’s been comfortable at a company for a long time may have forgotten the hustle it takes to be successful at a very early stage company.”
So instead of chasing after folks with big logos on their resume, look for these more critical signals:
Criteria 1: They’ve got early-stage experience
Nearly across the board, the folks I talked to said some startup experience is non-negotiable. “I need people who have done startup life before,” Michael Loiacono told me. (He adds bonus points if they’ve done both early-stage and growth stages, so they’re prepared for where you’re trying to go next.)
“And, no, saying that ‘it felt like a small startup inside a big company’ does not cut it,” he says. “You often don’t have marketing support. You have no brand recognition. You don’t have case studies. I need sellers who understand that the first 1-2 years are making something out of nothing.”
Becca Lindquist a specific example: “We hired a rep on my early sales team, and one of the first things he said was, ‘We’re charging way too little for this product. I’m going to go into these next three deals that I think we have a realistic shot at, and I’m going to double the price. Let’s just see what happens.’ Now, our price is higher (although not double) because of his experiment.”
The name of the game in early stage is trying something and seeing if I get my teeth knocked in. And if I don’t, then I’m going to keep doing it.
-Becca Lindquist, VP Americas at dbt Labs
It’s not simply about the resilience that early-stage startup life requires amidst the chaos. As ex-Figma Kyle Parrish explained, it’s also about whether they can be a clear and trusted voice in the feedback loop.
“Our CTO at the time, Evan, had probably never interviewed a salesperson before. But I spent a lot of time with him during the interview process learning about engineering’s value system and what he cared about. I think he was testing whether I could work well with other pieces of the company, because you spend as much of your time in the early days with engineers, designers, and product leaders as you do with customers.”
In early stage, everything is a tight loop. If you’ve only worked at companies where sales is on the 5th floor and engineering is on the third floor, you’re going to struggle.
-Kyle Parrish, Figma’s first salesperson
Criteria 2: They know your motion
As you set your sights on winning market share, finding someone who’s been in your domain for a while (and has a huge contact list to show for it) can be a tantalizing trap, as Jacquelyn Goldberg told me.
Here’s why it’s often such a misstep. “First, are they even going to be able to use their Rolodex when you’re so early and the product’s not stable? Second, what if you pivot after a month and decide you’re going after a new ICP? Now you’ve hired someone for a Rolodex you’re no longer using,” she says.
A Rolodex is the lowest thing on the list that you should be hiring for with an early sales hire.
-Jacquelyn Goldberg, VP of Sales at Sama
So focus on motion expertise, rather than domain experience, Kyle Parrish says. “If you're building a product-led growth business, you want someone who’s been on that journey. If your motion is purely top-down, don’t bring in someone who knows only 0-1 PLG,” he says.
If you can find someone who has domain expertise, that's always nice to have. But it's way more important to bring in someone who truly understands your motion.
-Kyle Parrish, Figma’s first salesperson
A caveat here is that there are some industries where past at-bats are more important. For example, the EvolutionIQ folks learned the hard way that they needed sellers with deep insurance experience. But even in those more entrenched industries, don’t let the stuffed Rolodex be the only thing you hire a seller for.
Criteria 3: They’ve been in sales leadership…and hated it
I really loved this tip from Michael Loiacono: “When I look at some of the top-end sales performers, a pattern I’ve noticed is that they’re very good at sales, but they’ve also tried leadership and decided it wasn’t for them. They don’t love managing other humans, they find they can be higher-impact in other ways,” he told me.
“I’ve had great success with hiring people who have tried management and tried leadership and then come back to being an IC. You may have to compensate them a bit higher because you're paying for their experience and leadership soft skills. But it’s well worth it.”
Criteria 4: They came in 2nd or 3rd place
There can be a halo effect when a candidate comes in with a hockey-stick growth startup on their resume — but tread lightly here, Varda’s Eric Lasker told me.
“I'd rather hire the salesperson from the second-best company rather than the first — that person probably had a 10x harder time than the person who was selling the category winner.”
-Eric Lasker, Chief Revenue Officer of Varda Space
It’s one way of testing for grit, which a few of the folks I talked to underscored again and again, including Michael Loiacono. “Simply put, I like people who’ve been through some shit, in their personal life or in business. This is a hard job and you will fail a lot — you need a thick skin, grit and resilience. The ability to get up and just keep going, with positivity and vigor, is a superpower. I don’t want the person who’s used to leads fed their way all the time and established brand credibility. That’s too damn easy.”
Criteria 5: They’re a missionary, not a mercenary
Both Kyle Parrish and Mike Molinet mentioned the same bit of phrasing, so it’s well worth repeating here: You want to make sure your early sales hires are missionaries, not mercenaries.
“Missionaries are here for the long haul — they want equity in the company, and they want to go execute on the lofty vision. Mercenaries are there for the $1M quota and their ability to go sell, sell, sell,” Molinet told me.
To separate the two camps, Sam Taylor told me to find common ground. “All of these companies that I’ve hopped into, I’ve at some point lived the pain of what they’re trying to solve. And I can articulate that in an authentic way. It doesn’t mean what you’re building is the hire’s entire passion and they think about cloud storage every night, but they should feel like they can be an ambassador for the change you’re trying to bring.”
Next up, we’ll unpack some of the interview questions and exercises that help get to the ground truth during your hiring process.
How do you evaluate talent? Beware the “chicken little” mindset
Coachability, resilience, self-awareness, passion — these are all non-negotiables when it comes to early-stage sales. But how do you actually test for these traits during the hiring process? Interviews alone are not enough here. “Salespeople will likely interview quite well, and will be polished — remember, they’re on calls all day,” says Sam Taylor.
To dig deeper, below are some of the go-to hiring exercises I heard. First Round’s VP of Founder Success & GTM, Emery Rosansky also generously shared her own sample sales candidate scorecard to add some rigor to the interview process:
Hiring exercise 1: Pitch me
This first one comes as no surprise to anyone who’s been involved in a sales interview loop — it’s an essential step. But whatever you do, do not ask them to pitch you the product they’re currently selling, says Mike Molinet. “I don’t care that you know something really well now. I’m trying to see if you’re able to learn and ramp up really quickly on a new thing.”
And Michael Loiacono recommends crunching the timeline significantly.
“I send the candidate an email with a handful of notes, the sorts of tidbits you might get from a discovery call (or through a GenAI tool now). There’s a bunch of information in there that’s really critical, and a bunch of stuff that’s probably noise. I ask them to come back and pitch me as if they’re a sales rep in 48 hours,” he told me.
This might sound like an absurdly tight turnaround — and that’s the point. “I’m not expecting them to pick up the ins and outs of the product in just 48 hours. If they really want the opportunity, they will have been doing their homework throughout the process,” he says. “So what I’m looking for is that you’re deeply passionate about joining this company. Are you going to grind for the next two days to get this in top shape? Is the deck going to look polished? Because in all likelihood, we’re not going to have a designer to put together a beautiful deck for you. Can you manage the meeting and lead me through a discussion that’s not just reading off slides? Can you watch the clock and not wait until minute 59 to ask me an important question?”
But, as he told me, the test actually starts before the pitch. “Do they ask smart questions ahead of time? I keep the exercise intentionally vague — I don’t give them a deck, I don’t give them a template. I just tell them my role and the company I work for as the buyer. I love people who are innately curious and are brave enough to ask what might seem like a stupid question,” Loiacono says.
I don’t over-index on your sales stats from your last two jobs, which are likely the result of a whole bunch of things outside of your sales chops. I don’t care that you were in President’s Club.
-Michael Loiacono, VP of Global Sales at Testlio
Hiring exercise 2: Demo me
Any candidates who made it past Figma’s early interviews were asked to turn around a complete demo of a mobile app created in the tool, Kyle Parrish explained. “We kept it very open and it was crazy some of the directions people took it. You saw the creativity and the curiosity. The people we ended up hiring, they all spent at least 10+ hours just learning the product.”
It goes back to the crucial ingredient that passion plays in the early-stage recipe. “You don’t have to want to be a designer. But if you don’t get excited watching YouTube videos, toying around with Figma, and seeing the potential of upending the status quo, then this is not going to be the job for you,” he said.
For the first almost three years and 25 sales hires, they would then present their demo to Figma’s founder Dylan Field. “It’s a pretty intense experience doing a technical demo with the founder of the company,” he admits.
Hiring exercise 3: The re-do
Parrish recalled one of his favorite demos that didn’t start out so polished: “Her first crack at the demo wasn’t great. But I could tell that she had a lot of potential. So I talked the team into giving her a second chance. I delivered the critical feedback from her first demo because I wanted to see how she reacted and then gave her a re-do,” Parrish explained.
The second time was the charm. “To this day, she gave one of the best demos Dylan had seen about the product. Her whole family came from a farming business in central California and she built a mobile app around the farming business. It was quirky and funny and it had so much passion and depth. It showcased her true potential — and she was still on the team years later.”
When you feel the gut instinct that there’s someone special, albeit not perfect, don’t be so quick to dismiss them. Because the interview process itself is imperfect.
-Kyle Parrish, Figma’s first salesperson
Becca Lindquist brings the re-run into every single pitch, regardless of whether the candidate nailed it the first time around. “I ask them to bring a persona of someone they’re currently selling to, and have them do a quick 10-minute roleplay. After the ten minutes are up I ask what they think they did well and what they would do differently, and then I share my own feedback,” she says.
Then, they re-run the exercise. “There are some people who can correct their mistakes on the spot and are excited to try again. There are others who are caught off guard and not excited about it. I’m looking for people who have self-awareness. Do they think they’re God’s gift to sales or do they say ‘I wish I had dug in a little more here,’ or ‘I should have been more prescriptive about next steps.’ And then on the re-run, do they actually correct their mistakes? That’s someone who learns quickly.”
Hiring exercise 4: The written take home
While presenting a demo or a pitch can give you a good sense of a salesperson’s IRL presence, remember that startup sales is not just about hitting your talking points on a Zoom call. Written communication matters, too. Asking the candidate to complete a written take-home exercise not only gives you conviction on their ability to convey clear thinking but also their attention to detail.
What I’ve found is that the key to a well-crafted take-home exercise is to make it a variant of something the seller would actually be doing in the job. And in my experience as a hiring manager, I find that take-home hiring exercises separate people who wouldn’t mind having the job from the people who really want the job.
I asked Emery Rosansky to share a few sample take-homes she recommends to give you a jumping-off point:
- After 3 months in your role, you realize that you have a 10% conversion rate from disco call to demo, whereas the founder has a 30% conversion. Why is your conversion low? How will you improve the rate? What can you do to go back to the 90% that didn’t convert?
- You’re trying to get a meeting with the CRO of Airtable. How would you tackle getting into this account?
- You have a 2nd call with the Airtable team with people you’ve met (CRO & Head of Enterprise Sales) and people you have not yet met (Revenue Ops & Data). How do you prepare for the meeting?
- You have a hot opportunity that has gone dark after 1 discovery and 2 demo calls. Why do opportunities typically go dark? How can you avoid this in the future? How do you bring the opp back to life?
Hiring exercise 5: The anti-sell
If I haven’t banged this drum enough, it bears repeating: early-stage sales is hard. And you want to be as honest about that as possible well before the hire takes their desk.
“I exhaustively paint a picture of the good, the bad, and then really emphasize the ugly. I want that person to be extremely clear about what it’s going to take. If they still sign up, that tells you a lot about their heart and mindset,” Michael Loiacono told me. “There’s no perfect job. Every job has some great parts and some crappy parts. And if you don’t dig deep into the crappy parts, all of a sudden those people come in and three months in are frustrated, and potentially even leave because the expectations were poorly explained.”
Candidates can smell when you’re painting a picture of rainbows and roses that’s too good to be true. I’d rather be honest about what the job is, what’s great about it and the big upside — but also what’s hard about it, and still have them come aboard.
-Michael Loiacono, VP of Global Sales at Testlio
Must-ask interview questions:
Finally, in addition to sharing my own favorite interview question, I asked the folks we talked to to share their favorites. Here’s what I recommend adding to your own interview loops — for an even more robust list of questions (with a bunch of additions from my friend Emery Rosansky), check out this doc.
- What’s your biggest concern about taking this job? I ask just about every candidate this question — you’d be shocked at how illuminating it can be. Sometimes candidates bring up a concern that is spot on, and I don’t shy away from it. I’d rather lose them now than three months after making the hire. Other times, the candidate doesn’t say anything, and that’s equally illuminating. They’re probably not being fully honest and just don’t feel comfortable giving feedback.
- What’s the oddest thing you’ve ever done to get a partnership across the line? “This question provides some insight on the candidate’s creativity and does a surprisingly good job of weeding out folks with questionable moral judgement,” says Varda Space’s Eric Lasker.
- If you were to start tomorrow, what’s the first thing you would do? “This tells me how scrappy they are,” says Michael Loiacono. “What are their expectations of support they’ll have in the role? How resourceful are they? I want people who can look at things realistically,”
- Tell me about the last thing you learned at your company, and how you went about learning it. “I’m looking for whether they’re going to fail alone,” says Becca Lindquist. “The best sales reps I know are moderately greedy with people’s time, especially when they’re onboarding. I’m looking for answers like, ‘Well, the first thing I did was I found someone technical and made them my new best friend so I could ask them all of my stupid questions.’ Can they build their own onboarding track and not fail by themselves?”
- What’s something outside of work that you are passionate about? “It could be roasting coffee beans, it could be making their own art. But I just want to find something they’re irrationally passionate about because that tells me they’re deeply curious. Some of the best people I’ve hired have these really niche hobbies,” says Mike Molinet.
- Tell me about a time something wasn’t going well at work. “You want people who are comfortable sharing feedback around what you can improve as a leadership team and a business. But true resilience is when folks can share feedback while also believing in the mission and the longer-term strategy and execution plan,” says Kyle Parrish.
- At our stage, we are sometimes selling customers on our ability to deliver on features promised in a roadmap. How do you think about selling roadmap items? How do you manage customers' expectations? -Emery Rosansky
- What’s a technical objection you’ve gotten in a previous role and how did you overcome it? -Emery Rosanksy
- As one of the first sales hires, you won’t have access to a ton of collateral or supporting material. How do you overcome this? -Emery Rosansky
- Walk me through the most complex deal that you closed in the last year. Share step by step how it got done. -Emery Rosansky
- Tell me about a time you lost a major deal. What went wrong? What did you learn? -Emery Rosansky
- What is your sales superpower? -Emery Rosansky
- What are you not good at / need coaching on? How would your last boss answer that question? -Emery Rosansky
And whatever you do, avoid at all costs hiring the folks who seem to rattle off all the reasons why their last product never found strong product-market fit, says Kyle Parrish.
It’s easy to get caught in what I call “chicken little syndrome.” There’s stuff happening in the macro environment, there’s stuff happening internally, and it’s easy to get spun out of control and think everything’s doomed and nothing’s working. Those people are toxic to your environment.
-Kyle Parrish, Figma’s first salesperson
How do you set them up for success?
Early startup hires, whatever their function, aren’t exactly expecting a robust and well-thought-out onboarding process (or at least they shouldn’t be). “My first day at PebblePost I walked in and got a laptop and that was about it,” Jacquelyn Goldberg told me.
There are a million things on the early-stage founder’s to-do list, and you’re probably eager to offboard sales as quickly as possible. But without some sort of ramp plan, even the just-right hire can wander off course quickly.
The folks I sat down with had different takes here. Some favored a more aggressive onboarding strategy, with a quicker time to start pitching customers (and a steeper quota to match). Others preferred to spend more time laying the foundation before letting a new rep get remotely close to a customer call.
I don’t think there’s any right answer here — it’s largely dependent on your product and motion. For example, if you have a technically complex product, sellers need more time to learn the ins and outs before getting on the phone with a technical buyer. Whereas if the founders have crushed their founder-led sales and have a repeatable process with a crisp message, early sellers can probably ramp much more quickly.
So instead of prescribing an exact 90-day onboarding plan, I’ve collected some of the tested strategies I heard in my conversations so you can pick and choose what makes the most sense for your circumstances.
But before we dive into that, there are a few onboarding non-negotiables, regardless of your motion or market:
- Set the right timeline. I liked this rule of thumb from Mike Molinet: “However long your sales cycle is, that’s approximately how long it should take until a sales hire is running completely independently. If you have a complex enterprise sales cycle that takes 9 months, it might take them 6-9 months to fully ramp.”
- Treat them like a fellow founder. “The more you bring them into conversations on the market, with the product and engineering team, even financial meetings with investors, they understand why targets are built and the state of the business. It’s all about giving people credibility so eventually they can speak like a founder and a business owner, not just as some guy who’s trying to hit a quota,” Mike Molinet also told me.
- Stay ready to unblock. Even when bringing on a sales hire, founders need to be game to participate, says Sam Taylor. “If I ask the CEO to come to New York for an important sales meeting, am I going to have to drag them kicking and screaming? Bret Taylor did an amazing job of this in the earliest days of Quip. Anytime we wanted to pull him into a deal he said yes. That doesn’t mean the founder will be involved in every single deal (and if you are, it’s time to think about parting ways with your sales hire). But don’t shut yourself off from this work entirely.
One of my key learnings on the transition from founder-led sales to hiring a sales team is that I, Sam Taylor, can walk into a room and say “This is the future of work.” And some people will say, “I don’t care — who the hell are you?” But Bret Taylor walks into the room and says this is the future of work, and everyone starts taking notes.
-Sam Taylor, former VP of Revenue at Loom
Now, onto some of the specific onboarding techniques.
Technique 1: Start on the support front lines
When Kyle Parrish joined Figma as the first sales hire, he was itching to start closing customers. So imagine his surprise when founder Dylan Field asked him to spend the first month with the customer support team. “He asked me to not do anything on the sales side but just to spend time in the support queue, working on bugs, understanding the ins and outs of the product,” Parrish says. “At first I was a little taken aback. I was just hired to help this team build their business, drive revenue, and hire a sales team and now I’m just working the support queue.”
But he gives Dylan props now — it was a stroke of onboarding genius. “I got to learn the ins and outs of the product at a level I probably never would have. And most importantly, I got the opportunity to develop a strong relationship with the support team out of the gate and laid the foundation for a different kind of sales team at Figma.”
Sometimes in those first 90 days you have to take 2 steps back to move 4 steps forward.
-Kyle Parrish, Figma’s first salesperson
“Early on I was trying to understand why these folks used Figma. At the time, there was still this fear that it was creepy to jump into a design file and see your manager or the developer that you work with when you’re not ready to share your design work. Sketch was the dominant design tool of that era and InVision was fast-growing,” he told us. “I was just understanding why these customers were even giving Figma the time of day.”
Michael Loiacono strongly agrees that new hires need time to make friends before they can make waves. “What people don’t realize is that so much of sales hinges on internal collaboration,” he says.
You want to have relationships where you can say, “I need your help solving this problem,” versus just being the quintessential sales guy pounding the table because they have a big deal that needs product support. That’s how sales gets a bad stigma.
-Michael Loiacono, VP of Global Sales at Testlio
Technique 2: Ride shotgun
Jacquelyn Goldberg’s onboarding at PebblePost left a lot to be desired — so she took the reins. "I had to create my own curriculum. So I asked the CEO to give me his LinkedIn login. I was able to look at the messages he was already sending to prospects and figure out the ICP we were going after. Then, I drafted more cold outreach emails for him and sat in on every meeting.”
She recommends a similar approach to other first sales hires to start off on sound footing. “That first month, I suggest the salesperson rides shotgun on everything — but that doesn’t mean the founder is doing all the work. The rep is sending the meeting invites, they’re doing the follow-up. The founder is just in the room doing the pitch.”
Technique 3: The week one demo
As Becca Lindquist told me, by the end of their first week every new hire at Heap had to do a demo in front of the rest of the team. “To deliver a strong product demo, you need to read through our customer stories, find relevant examples and learn what’s valuable to our prospective customers. You also probably need to talk to someone else at the company to find out the types of questions customers ask about,” she says.
In her experience, this demo exercise is an early test of both skill and will. “There’s the skill of whether they can pick up on the technical aspects of the product. And there’s also the will of whether they put a ton of effort into building a good demo,” she says.
Technique 4: Grade on learnings, not pipeline (at first)
As a general rule of thumb, Michael Loiacono wants new sales hires to stay far away from the phones. “What I don’t want is someone who’s in their first week and trying to get on the phone and close customers. In the early days, you usually can’t afford to completely blow those at-bats,” he says. “If they are talking to customers, I’d much prefer if they’re using that time to learn their world and painpoints.”
So resist the urge to pile on pipeline metrics. “I’d rather have my first quarter of targets be all learning-based. Because ultimately when I unleash that person, they’re going to be so much more effective with speaking to our buyers. When you’re a first seller, you’re as much of an evangelist as you are a salesperson.”
If you’re not clear on the problem you’re solving for your buyers, not a whole lot else matters. I don't want someone in a rush to get a bunch of leads just for them to get on the phone and make us sound less credible. Modern selling is brokered in trust.
-Michael Loiacono, VP of Global Sales at Testlio
Wrapping Up: An antihistamine for sales allergies
To close us out, I loved this story from Kyle Parrish’s In Depth interview — and I think it’s one that will resonate with a lot of other early sales hires. “My worst fears in building Figma’s first sales team was that we were going to be the suits coming in and we would be allergic to the culture that they already had,” he says.
But that ended up being far from the truth. “I came in and people were eager and curious — they wanted more customers to use the products. It was not this sentiment of ‘I’ve heard these horrible stereotypes about tech salespeople and now the company is going to start changing in a way that’s not something I want to be a part of.’”
He credits founder Dylan Field in a big way — with a small tactical tip that I think all founders should consider borrowing. “Dylan did a good job in our all hands meetings not just talking about company updates or a story from the engineering or product team. He paved the way for us to tell stories early on — we called it ‘sales tales,’” he explained.
And for first sales hires who get this spotlight, Sam Taylor reminds them to use it wisely: “I’ll never forget being at Quip and a sales guy presented at an all-hands meeting and it was just like, boom, acronyms: ACV, ARR, AE, whatever. An engineer pulled me aside at lunch and said, ‘I want to be excited about what he’s talking about, I just have no idea what he’s saying.’”
Early sales hires: You’re not sitting in the sales den at Salesforce anymore. You’re one of the only people in the GTM function. That means your job is to be a translator between the market and the rest of the company.
-Sam Taylor, former VP of Revenue at Loom
For as much as we’ve discussed the dismal odds of long-term retention when bringing on your first revenue leader, I want to end on a note of optimism. Yes, it is a complex hire to nail — but when done thoughtfully, the right sales leader can be a remarkable inflection point in a startup’s trajectory, cranking up the volume on what was once a low hum of customer traction. So take the time to find the right person (and don’t give in to pressure to hire someone just because your investor thinks you should), set them up for success, and stay heavily involved in those critical early months.
Be sure to follow along with this series — we'll be diving deep into more early-stage GTM topics like how to find your ICP, design partnerships, getting your pricing right, and much more. (You can catch future pieces by subscribing to The Review or following me on X @BigMekaStyle).