I've hired over 60 account executives in the last three years.
I've failed a lot. Bad hires that cost us quarters. Candidates I let slip because I wasn't paying attention. Roles I filled with the wrong profile because I hadn't done the work to define the right one.
I've also gotten it right.
At Flock Safety, we built a new segment from 0 to 50 reps in 7 quarters.
At Edia, we are building an elite sales team at a Series A edtech company — a vertical that most AEs laugh at — by going on offense, being ruthlessly specific about who we want, and treating recruiting the way the best AEs treat pipeline generation.
This post is everything I know. Soup to nuts.
If you're a founder hiring your first sales team, or a VP trying to scale from 3 AEs to 15, this is for you.
The truth nobody teaches you
When I took my first sales leadership role, I thought the most important thing for me to do was to help reps close deals, with a secondary importance on pipeline generation and forecasting.
However, the more experience I gain — and the more AI removes the friction to operational challenges — I have come to believe that the single most important activity of a sales leader is to recruit elite talent.
Recruiting talent is something that should never be outsourced to job postings and talent acquisition teams. Those things can help, but they should be a cherry on top, not the sundae.
Most sales leaders spend 80% of their time on the right side of the equation. They coach. They run deal reviews. They inspect CRM hygiene. They shadow calls. All good things.
But they treat recruiting like something that happens when a seat opens up. Or worse, something that the TA team owns. That's backwards. Recruiting is the multiplier.
Get it wrong and everything downstream gets harder. Get it right, and you're coaching people who don't need much coaching.
Poor recruiting is the most common reason sales leaders fail. I've watched it happen. I've experienced it myself.
Only the hiring manager can do it well. Not your recruiter. Not HR. Not a third-party search firm.
You.
Delegate this, and you're outsourcing the most important decision you make.
Before you source a single name: get aligned
Most leaders start recruiting before they've answered the foundational questions. I've made this mistake. You source 50 candidates and get to the final rounds before realizing your comp structure is wrong, or you're hiring for the wrong segment, or your quota is too aggressive to attract the person you actually need.
Do this work first.
- Align on your 24-month target. What does the number need to be? Work backward from there.
- Align on segmentation. Are you hiring Enterprise, SMB, or both? These are different profiles. Do not conflate them.
- Align on quota and OTE by segment. What's the quota? What's the OTE? What's the bookings-to-OTE ratio? If you can't answer these clearly, you're not ready to hire.
- Align on ramp time. Enterprise ramp is typically 6–9 months before full quota. SMB might be 3–4. Model this. It matters for when you hire, not just how many.
- Build the capacity model. Now you know the number, the segment, the comp, and the ramp. Back into how many reps you need and in what sequence. Hiring 5 people at once is usually worse than hiring 2 strong people early. Sequence matters.
Only after this do you know what you're looking for.
Step 1 — Identify: Nail the ideal rep profile (IRP)
This is where most leaders fail. Not because they don't have a profile — they do. It's just wrong.
The classic mistake: searching for a unicorn without knowing what kind of unicorn. I want a $1M closer who'll relo, take a pay cut, thrive in ambiguity, and be excited about a market they've never sold into. That person exists. But you've made the search 10x harder, and you've probably talked yourself into hiring someone who checked 4 of 5 boxes and will struggle on the 5th.
The way to build the right IRP: study your current team. Who's succeeding? What do they have in common? Who's struggling and why? What job do you actually need done: a hunter who figures it out, or a strategic relationship player with existing relationships?
The book Who changed my mindset on hiring. The author talks about how to build a JD with specific outcomes and activities needed to weed people out early. He also stresses the importance of matching your profile to the stage of your company and continuing to iterate as you grow.
- 4+ years full-cycle experience
- 2+ years at the same company (no job hoppers)
- At least one Series A–C experience
- High slope — at least one promotion. Trajectory matters more than where they are today.
- Geo: HCOL cities — LA, SF, Austin, SLC, Denver, Phoenix, Chicago, NYC, Boston. Cost of living creates hunger.
- Current company: SaaS, high-tech, AI
- SLED-adjacent okay if high-growth (e.g. Verkada, Peregrine, MagicSchool)
- Bonus: ex-teacher
Tangibles to look for
- Slope over intercept. A rep at $180k OTE with two promotions in three years is more interesting than someone at $250k who's been flat for four years.
- Hunter DNA. Loves pipeline generation. Loves building from nothing. Gets energy from new logos, not farming existing accounts.
- Evidence of qualification. Do they know what a champion is? Can they articulate why a deal is good or bad? Have they used MEDDPICC or anything like it?
Intangibles to look for
Intelligence, Drive, Coachability, Character.
I rank them: Character first. Drive second. Intelligence third. Coachability fourth. But this is worth thinking hard about for your specific stage. A founder hiring rep #1 might weigh this differently than a VP hiring rep #15.
Too coachable is a real thing. A rep who just nods and agrees with everything you say isn't going to push back on a bad deal or tell you when the territory is broken. You want someone who can be coached and has a spine.
How to actually read a LinkedIn profile
- Start from the bottom. Work up. You want the progression to tell a story.
- Look for evidence, not just titles. Did they get promoted? Did they show numbers in their descriptions?
- Look for unexplained gaps. Not a dealbreaker, but worth asking about.
- "People Also Viewed" is underrated. LinkedIn is telling you who looks like this person. Free IRP sourcing.
- Check mutual connections. Back-channel intel before you even get on a call.
- Discount Skills & Endorsements entirely. They mean nothing.
- Attention to detail in their own profile is a signal. Typos in their bio. Incomplete profile. These things matter.
Step 2 — Attract: Go on offense
Here's the thing about recruiting at a Series A that no one wants to hear:
And here's the asymmetry that most leaders don't use: it is rare for an actual hiring manager to reach out to an AE. Recruiters reach out all the time. Generic InMails are noise. But when the hiring manager sends a personalized note? Response rates go through the roof.
We hired 8+ AEs cold at Edia — a Series A edtech company that most AEs had never heard of — by going on offense against our IRP.
Sell first. Qualify second.
Most leaders do this backwards. They lead with "Are you open to new opportunities?" They ask about compensation in the first message. They disqualify before they've even created interest. That kills the conversation before it starts.
The anatomy of a great InMail
-
Personalize. One sentence. Something specific to them — their company, a promotion you noticed, a mutual connection, a post they wrote. Signals you're not blasting a template.
Example: "I saw you made the jump from SDR to AE in under a year at Datadog. That kind of slope is exactly what we look for." -
The hook. This is where most leaders go wrong. They talk about their company. The rep doesn't care about your company yet. They care about their career and their earnings. Lead with what's in it for them.
For Edia, our hooks are: K-12 is under 2% penetrated. Over 50% of our pipeline is six-figure deals. Series A — maximize W-2 before the equity story gets crowded. Second product went $0→$1M in 5 months. Backed by Felicis, 8VC, Susa. Clear path to management. - The 8 Mile move. Name the objection before they raise it. For us: "I know what you're thinking. EdTech? That's a space for teachers, not sellers." Then flip it. "No one thought restaurant POS was a gold mine. Then came Toast ($24B). No one thought HVAC software could scale. Then came ServiceTitan ($10B). Math homework is next."
- Clear call to action. Not "let me know if you're interested." Give them something specific: "Do you have 20 minutes on Thursday or Friday?" One question. One ask.
Know your three whys cold
- Why this company?
- Why this role (and why you specifically as a leader)?
- Why now?
Practice these until they're effortless. This is your recruiting pitch. The same way a great AE has a crisp answer to "why are people buying this?" — you need a crisp answer to "why should I come work for you?"
The recruiting funnel
Most leaders have no idea what their recruiting funnel looks like. They do a burst of outreach when a seat opens, get discouraged when the pipeline is thin, and wonder why they can't close candidates.
If you need to hire 5 reps in 5 weeks, you need 500 InMails in flight immediately. That's not a sprint. That's a system.
Track this weekly. InMails sent. Responses. Screens. Qualify calls. It's a pipeline. Manage it like one.
If your funnel is thin, you have a volume problem or a message problem. Figure out which one.
Step 3 — Qualify: Nail the interview process
Five stages. Each has a clear purpose.
First filter. Basic fit, interest, logistics. Most importantly: keep selling. Don't flip into full interrogation mode before you've established genuine interest.
Pipeline Generation
- Tell me about the composition of your book. How much net new versus existing?
- Where do leads come from? What percentage is self-sourced?
- How do you plan your week?
- What are your top three target accounts right now, and who specifically are you targeting at each — and why that person?
The last question is the tell. A vague answer ("whoever is the decision maker") means no disciplined outbound motion. A specific answer about a VP with a named business problem means they know how to hunt.
Champion Building
- Who's the champion you're most proud of building? Walk me through it.
- How did you build them? How did you know they were a real champion and not just a friendly coach?
Listen for specificity. "I built a great relationship with the principal" ≠ "I knew she was a champion when she sent me the internal slide deck from their budget meeting unprompted."
Qualification
- How do you know if a deal is good or not?
- What criteria matter when evaluating whether to push or disqualify?
- What's the top reason your deals go closed-lost?
The best answer to that last question involves self-awareness — not "competition undercut us on price," but something like "I waited too long to identify a real champion."
This is the most important stage. Take your time here.
Drive / Grit
- Tell me your story. Push on the circumstances — don't accept a resume recitation.
- Why did you leave that job? What led you to make that move?
- What's the hardest thing you've ever had to do? Not in sales — in life.
Look for a chip on the shoulder. Reps who are running toward something are good. Reps who are running away from something are often better.
Intelligence
- Can they explain what their companies do in simple terms — not jargon?
- Can they connect facts to conclusions? If they did something, do they know why it worked?
- Can they articulate the insight, not just the action?
Character
- Tell me about a deal you lost because of something you did or didn't do.
- If I asked one of your teammates to describe you in three words, what would they say?
- Who are the top three people you work with? Would you mind if I reached out to them?
That last question is a test. The rep who hesitates — that's data. The rep who immediately gives you names and says "please do, they'll tell you everything" — that's also data.
Coachability
- What's the most impactful piece of constructive feedback you've received from a manager?
- What's an area of your sales game you know you need to improve — and what have you done about it?
Red flag: "I can't think of any real feedback, I've always exceeded quota." Every rep has something. If they can't name it, they're either not self-aware or not being honest.
- 15 min: Walk me through your territory attack plan for our market.
- 20 min: Role play. I'll be the prospect.
- 10 min: What feedback do you have for me? What questions do you have about the role, the company, the leadership?
That last piece — the candidate's questions — is one of my favorite signals. The rep who asks sharp, specific questions about attainment, top performer success, and product roadmap is someone who's evaluating you the way you're evaluating them. That's who you want.
Culture: Will they thrive in high-growth, high-ambiguity? Give me an example of when you had to pivot fast because the business changed underneath you. What do you do to continuously improve your sales skills?
Commitment: Are they here for the mission or just the paycheck? Why this role, why now, where do you see yourself in three years?
At Edia, the mission is to change the life trajectory of every student in America. When a candidate lights up at that — when they have something real to say about education or about a teacher who changed their life — I pay attention.
The thing I wish I'd known earlier
Recruiting is pipeline generation for a sales leader. That reframe changed how I operate. Our team blocks time for it. We track it weekly. We don't wait until a seat opens. My team is always building a bench.
Always be recruiting. Celebrate your recruiting wins with your team the same way you celebrate closed deals. Make it a metric.
And remember: the candidate you're talking to is evaluating you as much as you're evaluating them. How you show up in this process — the thoughtfulness of your outreach, the quality of the conversation, how you handle their objections — that's the first signal they get about what it's like to work for you.
Make it a good one.