The Founder‘s Guide to Hiring Your First VP of Sales in 2024
Hiring your first VP of Sales is one of the most consequential decisions a startup founder will make. A great VP can unlock step-function growth, while a bad hire can set you back quarters and cost you millions.
As we enter 2024, the market for top sales leadership is more competitive than ever. Startups need a world-class gameplan to attract and close their ideal VP. Here‘s how to do it right.
When to Hire a VP of Sales
Founders often agonize over the timing of their first VP Sales hire. Hire too early and you risk wasting precious resources. Hire too late and you may plateau without experienced leadership.
So when is the right time? Most experts agree you should hire a VP Sales once you have:
- $1-3M in ARR
- 5-10 sales reps
- A repeatable sales process
- Healthy unit economics
- Steady stream of inbound leads
One study of 100 top SaaS startups found the median hiring time was 2.5 years after founding, with an average ARR of $2.1M. Another survey pegged the ideal range at $1-5M in ARR.
Ultimately, the trigger is less about hitting a magic revenue number and more about having found product-market fit and a repeatable GTM motion. If you‘re ready to pour fuel on the fire, it‘s time for a VP.
What to Look for in a VP of Sales
Not all VPs are created equal. A rockstar at an established company may flop at an early-stage startup. You need someone purpose-built for the chaos of zero to one.
Key Qualifications
- 7-10+ years of SaaS sales leadership experience
- 3+ years in management role at a startup with $1-20M ARR
- Track record of scaling sales team from 5 to 25+ reps
- Consistent quota attainment and revenue growth in previous roles
- Expertise with key SaaS sales motions (inbound, outbound, etc.)
Crucial Characteristics
- Passion for recruiting and developing talent
- Hands-on closer who leads from the front
- Strategic thinker who can build a GTM plan
- Analytical and metrics-driven
- Inspiring leader who earns trust and respect
- Collaborative cross-functional partner
- Willing to get hands dirty and figure it out
According to a profile of 50 successful startup VPs, the most common backgrounds include:
- 4-5 years as a Director or VP at a similar stage startup (72%)
- Consistent 100%+ quota attainment as a frontline manager (64%)
- Experience managing 20+ reps and $10M+ revenue (55%)
- Built and scaled 2+ sales teams from scratch (48%)
Resist the allure of brand-name hires from Google or Salesforce. Find the hungry up-and-comer who has lived the journey you‘re about to go on.
Key Responsibilities of a VP of Sales
So what does a VP Sales actually do all day? Buckle up, because it‘s a lot. Here‘s how most VPs spend their time:
| Activity | Early-Stage | Mid-Stage |
|---|---|---|
| Recruiting | 35% | 15% |
| Rep Coaching & Enablement | 25% | 15% |
| Process & Plays | 15% | 20% |
| Strategy & Planning | 10% | 25% |
| Closing Deals | 15% | 5% |
| Cross-Functional | 10% | 20% |
Recruiting Machine
In the early days, recruiting is the #1 job of a VP Sales. They should be spending up to 50% of their time sourcing, interviewing and closing top talent.
As Jason Lemkin says, "Nothing else matters if you don‘t have the right team." A players hire other A players, so nailing those first 2-3 hires is critical.
Sales Whisperer
Coaching and enabling reps is priority #2. A great VP is constantly in the trenches – reviewing pipeline, role playing calls, and strategizing key deals.
According to one study, the average VP spends 30-40% of their one-on-ones on opportunity coaching. The best ones do it daily, not just in a weekly meeting.
Process & Playbook Engineer
Every startup needs to find a repeatable sales process. That‘s where the VP comes in – designing playbooks, scripts, battle cards and email templates.
In a survey of 30 top VPs, 92% cited "sales process optimization" as a top 3 priority in their first 90 days. You can‘t scale without a machine.
Strategic Architect
As the company grows, the VP must focus more on go-to-market strategy. What segments should we target? What channels and tactics? How do we layer in partners, customer success, revenue ops?
The best VPs are always thinking 2-3 steps ahead. According to one study, they spend up to 50% of their time on strategy vs. only 25% for average performers.
Deal Closer Extraordinaire
In a pinch, a great VP is also a world-class closer. When a huge deal is on the line or an important renewal is at risk, you want them riding shotgun.
One analysis found top VPs directly influence up to 70% of early-stage revenue via deal closing. But beware the VP who closes everything themselves – you want a teacher, not a hero.
Running an Effective Hiring Process
With such an important hire, you can‘t afford to wing it. Here‘s how to run a world-class process:
Write a Killer Job Description
Start by aligning on what you‘re looking for. Write out the key activities, qualifications and characteristics in detail. Be specific on stage, ARR experience, team size managed, etc.
Engage a Specialist Recruiter
Unless you have a deep bench of sales leader talent, lean on experts. Sales-focused recruiters know the landscape and can surface the best passive candidates you‘d never find yourself.
Define Your Interview Process
Map out stages, interviewers and key questions. Probe into their experience building teams, their leadership style, and how they partner cross-functionally. Go deep on specific deals and initiatives.
Include a 30-60-90 day plan presentation to assess their strategic thinking. Have them role play coaching a struggling rep to see their people skills live.
Sell the Opportunity
Don‘t forget you‘re competing against dozens of other companies. Share your big vision, the potential to make real impact, and why your startup is a rocketship. Introduce them to the founders and team.
Check References Thoroughly
Once you have finalists, go deep on references. Talk to former bosses, peers and direct reports. Probe for strengths and development areas. Ask would you hire them again – and watch for the pause.
Make a Competitive Offer
Finally, step up with a compelling offer. Assume you‘ll have to pay at the high end of the band. Offer meaningful equity with a clear path to growing their role as the company scales.
Mistakes to Avoid
Even the most diligent founders can stumble when hiring their VP Sales. Some common pitfalls:
Hiring a Rolodex
Beware the candidate who promises to "bring a huge Rolodex." Sales is about process, not relationships. You need someone who can build a sustainable pipeline engine, not dial up their buddies.
Overvaluing Closing Skills
Yes, you want a VP who can close. But you‘re hiring a leader to build a team and a process, not a solo superstar. Optimizing for closing quotas is shortsighted.
Mistaking Rep Skills for Management Skills
Many founders hire their best performing rep into the VP role. This rarely works – closing deals and building teams require very different skills. Look for a proven leader, not just a seller.
Skimping on Compensation
Trying to lowball on salary or equity will come back to bite you. Expect to pay top of market to get a true A player – the ROI is worth it. Don‘t lose a great candidate over a few thousand dollars.
Misaligning on Expectations
Be crystal clear on your expectations for the first 3, 6 and 12 months. Define what success looks like in terms of pipeline, revenue and team size. Make sure you‘re fully aligned before signing.
Your Next Move
Hiring your first VP Sales is hard. There‘s no magic bullet, but following this blueprint will stack the odds in your favor:
- Hire at the $1-3M ARR inflection point
- Look for a proven startup leader with a track record of scaling
- Prioritize recruiting, coaching, process building and strategy
- Run a rigorous, disciplined hiring process
- Align on expectations and set them up for success
Do it well and you‘ll find a true partner to help take your sales org to the next level. Get it wrong and you‘ll be back to square one. No pressure, but the future of your company may depend on it. Choose wisely.
