Why is hiring good sales leaders important for your business?

Sales leadership transforms potential into performance – the best product can’t win in the marketplace on its own, but the right team can. Hiring the right sales leader can become a turning point that empowers the business to start achieving its goals.

A good leader gets the most out of a sales organization – great sales leaders don’t just manage reps; they build, optimize, and run the machine to complement your stage of business. A strong sales leader should provide:

A clear, customer-aligned sales strategy
A defined process that’s repeatable and measurable
A hiring and onboarding plan to ramp new reps efficiently
Forecasting, metrics, and reporting leadership can trust
Ongoing coaching to turn potential into performance
Comfort in ambiguity (they come to the table with ideas and plans, not waiting to be told what to do)
A forward-thinking mindset (embracing AI to drive efficiency while doubling down on the human side of sales that builds trust and drives outcomes)

They are a critical strategic partner for other leaders – hiring a sales leader enables CEOs and founders to take a step back from the day-to-day operations of the business and stop carrying the weight of GTM alone. In addition, experienced sales leadership can drive cross-functional alignment, inspire teams across the organization, and build trust with critical customers.

Investors prefer an environment that purposefully creates conditions of growth – bringing on a sales leader de-risks growth and builds a repeatable engine that will allow the business scale beyond the founding team. Instead of taking a reactive, “luck-driven” approach to sales, the company can become proactive and intentional.

What are the different “types” of sales leaders, and when should you hire for each?

The ideal “type” of sales leader depends on your current problems – identify the most important things you need done and hire accordingly. Don’t hire a sales leader for the problems you hope to have someday. The most common reason a leader fails is because the scope wasn’t right – not because they are a bad leader. There is no such thing as a “catch-all” sales leader who is the perfect fit for every situation because nuance runs deep, and what works at one stage will break at the next. For example:

The right leader for a US-only team might not be able to manage global expansion.
The right leader for an enterprise outbound sales motion might not be right for a high-velocity SMB inbound motion.
The right leader to build a pipeline from scratch is not the right leader to scale a partner-led motion.

Note: very few sales leaders can take you from $10 – $100MM in revenue – the problems faced and the skills required at these 2 stages are vastly different. If your goal is to make the jump from $10MM to $100MM, determine what type of leader can start you on this journey, then reassess your needs as the org grows.

The 6 Types of Sales Leaders and When to Hire Each
Leader Type	When to Hire	What They Do
Foundation Builder	You’ve got early revenue and signs of product-market fit, but the sales motion is still scrappy or founder-led.	Build the sales engine from scratch: • Define process, refine ICP, create messaging, implement CRM, and close early deals. • Lay the groundwork for what repeatability could look like.
Stabilizer	Sales is happening inconsistently. Some things work, but execution is chaotic or the team isn’t set up right.	Diagnose gaps – across people, process, and performance. Restructure – the team, adjusts comp plans, and ensures the right people are in the right seats. Anchor – the org so it can scale with intention.
Expander	The foundation is working, and it’s time to grow into new markets, add reps, or increase coverage	Add infrastructure – establish Sales Ops, onboarding programs, enablement, and middle management. They also often create layered support functions and a formal team structure.
Integrator	Sales is siloed, misaligned, or out of sync with Product, CS, or Marketing.	Connect go-to-market efforts across departments by: • Strengthening internal handoffs • Translating customer feedback upstream • Driving alignment across the company. Note: integrators often excel in complex environments or post-merger scenarios.
Scaler	You’ve reached approximately $20M in ARR and need to professionalize the org for the next stage of growth.	Prepare for and drive growth by: • Building the leadership layer • Hiring and developing frontline managers • Owning forecasting and revenue planning • Building territory and org models • Playing a strategic role across the executive team and board
Turnaround Leader	Growth has stalled or is in decline. The team is misaligned, morale is shaky, and confidence is fading.	Assess and fix – audit what’s broken, realign priorities, restructure the org, and stabilize revenue. Bring earned knowledge – leverage deep experience in turnaround and change management. Handle critical situations with care and reliability – act with urgency to restore traction and trust.

Note: don’t let titles fool you – sales leadership roles come with a variety of titles (e.g., Head of Scales, Director, VP, CRO, “player-coach”, etc.). Focus on the jobs to be done, not the title.

Preparation & Timing

What do you need to have in place before hiring? When is the right time to hire a true sales leader?

Most early sales breakdowns are caused by foundational ambiguity, not a lack of sales reps – a rep can’t fix what isn’t defined. Don’t bring new hires on board until you have clear product-market fit, positioning, buyer personas, and GTM focus. Use the following checklist to determine if you’re ready to set a new salesperson up for success:

You’re solving a real problem, not just hearing polite interest
You’ve validated who the buyer is and how they buy
You can articulate the pain, not just the product

Hire a true sales leader when:

You have around 5 AEs (or equivalent selling capacity) and can’t lead them all yourself
You’ve moved beyond early traction into something repeatable and want to scale
The sales strategy needs more rigor and ownership than you can give it
You’ve validated product-market fit and now need someone to build the structure for growth

Note: a sales leadership should not validate the market for you – it is the founder’s job to validate product-market fit.

How should you approach making your first few sales hires?

Always start with founder-led selling – no one understands the customer, product, or problem better than the founder. Founder-led sales isn’t a step to skip. It’s the most important part of validating product-market fit. Nobody else can do a better job of figuring out:

Who your buyer is (and isn’t)
What objections come up and why
How customers want to buy (e.g., which systems are easier for you vs. create a better experience for the customer, and where should your process land?)
Whether your product solves a real, urgent problem

Once you’ve found traction, the founder’s role should evolve (not disappear) – exploratory founder-led selling should result in effective messaging and an emerging strategy for how to sell your product. The ideal progression looks like this:

Founder-led – the founder is doing the selling, getting reps in, and learning what works
Founder-managed – the founder brings in a rep or two and starts building around what’s been proven, while still staying close to the customer
Sales-led – once you’ve validated the motion and need help scaling, bring in a leader to build the structure, team, and repeatability

Caveat → the founder or CEO should never completely abandon what’s happening in sales. It’s how the business makes money, and it’s how you stay close to the heartbeat of the customer, even when you’re not directly involved in deals.

When should you hire an AE, a player-coach, or a true sales leader?

Identify the problem you’re solving before you build a hiring plan – there is no one-size-fits-all best practice for when to hire for certain roles. Focus instead on the problem you need to solve and what type of person/role can help you solve it.

Note: a useful signal in determining your next hire is what starts to break when the founder pulls back.

What will break?	What need does this break reveal?	Next hire
Execution	You need someone to run the play.	AE
Strategy	You need someone to build the playbook	Sales Leader
Team momentum	You need structure (e.g., what to do, how to do it, who owns what, and the rules of engagement) and a leader to enforce it.	Sales Leader or Manager
Internal coordination	You need someone to own deal follow-up, pipeline hygiene, or cross-functional handoffs.	An assistant, RevOps, or marketing support

Be wary of the player-coach trap – the idea of having one person to sell and lead sounds efficient, but it typically ends up creating confusion, misalignment, and missed targets. This approach rarely goes according to plan because:

Selling and managing are two entirely different full-time jobs.
Most player-coaches lack the time or experience to do either well.
There’s a built-in conflict of interest: they’re setting comp, managing territories, and coaching reps while also competing for the same bookings.
Ask yourself:

Remember that headcount isn’t the only bottleneck for a growing sales team – in some instances, it makes sense to expand leadership before growing the rest of the sales team. If your real blocker is a lack of leadership, clarity, or the “glue” holding the org together, a leader is better suited to solving the problem than an AE.

Scaling Your Team

How might the rest of your sales org scale as you add AEs?

More infrastructure is needed as your team of AEs grows – set the team up for success by providing the tools, leaders, and processes they need to scale effectively.

0-5 AEs: Founder-Led and Tightly Managed
Description	Founders can manage up to 5 AEs, but must treat sales as a full-time job and not a mere “task”. Reps look to the founder for everything including comp questions, deal support, forecasting, CRM issues, strategy, feedback, and prioritization. Note: the pressure typically starts to build once a founder manages 3 AEs.
Trigger(s)	You become a bottleneck: • Your calendar is out of control • 1:1s get bumped • Escalated sales calls have to wait • The team needs more support than you can realistically give (or know how to give)
Team vs. Founder Responsibilities	The right support can help with: • Scheduling, reporting, CRM hygiene, and internal coordination • Serve as a go-to for reps so you are not fielding every question • Keep things moving while you stay focused on strategic execution • Territory mapping and rules of engagement Other support can provide breathing room at this stage – a RevOps consultant, team lead, or assistant can take some responsibilities off the founder’s plate if you aren’t yet ready to hire a sales leader.

~5 AEs: Add Your First Sales Leader
Description	Once you reach five AEs, managing them yourself becomes unsustainable. The sales “machine” works, but it is fragile and requires coaching, more active management, process development, and momentum support.
Trigger(s)	Team support, rep performance, pipeline/forecast, repeatability, or sales strategy starts slipping.
Team Leader Responsibilities	A Version 1 Builder must have previous experience helping a sales org stabilize and grow. They will: • Own team performance and 1:1 coaching • Establish accountability rhythms and reporting • Take on hiring, onboarding, and territory management • Ensure the reps have a system to follow and a leader to lean on • Develop and drive the strategy, forecast, and continue to optimize it for improved outcomes and impact They must also lead Customer Success (which should now be in place) – if you don’t have CS by this stage, implementation is a mess, the customer experience is questionable, expansion stalls, onboarding suffers, and churn creeps in before you even notice. Full-cycle AEs that are responsible for both landing and retaining accounts require a leader with experience leads teams that touch the full customer lifecycle.

6-10 AEs: Add RevOps and Enablement
Description	Your team is ready to scale and requires more extensive and specialized support to grow in an efficient and effective way. Formalized structure, tooling, and internal alignment gaps start to materialize.
Trigger(s)	Teams start operating in silos and you no longer trust the data or process.
New Team Responsibilities	RevOps or Sales Ops – own tooling, reporting, territory planning, and pipeline visibility. Enablement – standardizes onboarding, tool use, messaging, and ongoing training. Note: if Customer Success is not in place by now, prioritize establishing a CS team before adding more sellers.

Beyond 10 AEs: Specialization and Leadership Layering
Description	You need an operating structure that can handle complexity and scale with intention.
Trigger(s)	Growth creates more issues/ confusion than success/ clarity: • Deals slow down • Roles blur • Leaders are stretched too thin • There are more questions than answers • The strategy is falling short consistently (beyond one quarter) • GTM feels misaligned
New Role Responsibilities	Define roles and invest in leadership that support the people, process, and delivery challenges of a growing org – key roles might include: • Sales engineers and solutions teams – for complex and technical deals • Implementation and account management teams – to support onboarding and expansion (depending on CS and customer demands) • Segment-specific AEs – across SMB, Mid-Market, Enterprise, Global, Channel, or Partnerships, each with their own leaders • Regional or vertical teams – that require tailored strategy, culture, and oversight You might also bring in a VP, SVP, or CRO – this role will unify the entire GTM org, prevent silos, and drive company-wide alignment.

Hiring Strategy

Where should you look when hiring sales leaders?

Tap your network, but don’t let familiarity compensate for qualification – having a network is valuable, but just because someone is within reach doesn’t mean they are right for the role. The bar should stay high no matter how you meet the candidate.

Ask for referrals – lean on investors, advisors, operators, and founders who have hired and worked with sales leaders at your stage. Referrals can surface strong profiles quickly, but only if they come from people who understand what success really looks like in your world. And even then, your work is not done. You still need to dig into:

The content (what’s on paper)
The context (stage, scope, complexity)
Their actual competence (what they’ve done, how they think, and how they execute)

Search inside Slack channels and trusted communities – Slack groups and founder/operator communities can be great sources of talent. You might hear about someone before they hit the open market. But again, you need to filter for fit. Not just engagement, energy, or a good story. Treat every candidate like a serious investment and take them all through the same hiring process.

Get recruiting help if you need it – hiring an executive sales leader is high-stakes, time-intensive, and full of nuance. If what you’ve been doing isn’t working or you’re not confident in your ability to lead the process, properly vet candidates, or translate surface-level traction into long-term success, get help.

Note: you can’t hire well if you don’t know what you’re solving for – if you aren’t clear on the actual job to be done, the results required, or the environment this leader will need to succeed in, you’ll default to the wrong signals (e.g., charisma, pedigree, or past company logos). If you are not sure if you can tell the difference between potential and performance, hit the pause button.

What should be in your hiring scorecard? How does it differ by company stage and type of sale?

A great scorecard keeps your hiring focused on what matters most – it forces clarity on what you need the person to do, and whether they can do it. The right scorecard depends on your stage, your customers, market dynamics, team infrastructure, and your business reality.

The 5 table stakes for any sales leader – no matter your stage, there are 5 core areas that should be on every scorecard when hiring a sales leader. These are your non-negotiables. If these are missing, nothing else will stick:

Urgent superpower fit – every strong sales leader excels in one or 2 specific things– not everything. Some are builders. Some are scalers. Some are turnaround operators. Your scorecard should force clarity on the most urgent superpower you need based on your stage. Don’t hire a maintainer when you need a builder. Don’t expect someone to scale if they have only ever executed someone else’s playbook. See more on superpowers here.
Cross-functional collaboration – sales does not operate in isolation. If your leader only knows how to think like a sales rep or shows up with a “sales versus the world” mindset, it will backfire fast. This role must know how to partner across Product, Marketing, CS, Finance, and RevOps to drive revenue outcomes together.
People-first leadership – your sales team is not a number on a dashboard. If a leader only focuses on metrics and misses the people behind the performance, you will churn talent. And it will cost you seven to eight figures. You need someone who can recruit, coach, retain, and elevate others (even if that’s an executive leader of other leaders). That is what drives real performance.
Clear, confident communication – this role is highly visible. They need to be able to present to the board, write clearly, manage up, and hold tough conversations with customers and peers. They can back up their words with meaningful action and proactively expectations up, across, and down the org. Weak communication leads to confusion, lost deals, and eroded trust.
Forecasting competency – if they cannot forecast, they do not know how to run the business. Forecasting is not just a spreadsheet skill. It reflects how deeply they understand pipeline, performance, and patterns across the org.

Incorporate additional areas based on your stage and sale type – consider adding 5-8 role-specific areas such as:

Growth Stage Experience (0 to 1, 1 to 10, 10 to 50, 50 to 100, pre-IPO, and beyond)
Sales Process Ownership (Have they built one? Scaled one? Operated within one?)
Builder vs. Maintainer (What are you solving for?)
Hiring and Retention Strategy (Can they attract and grow talent that sticks?)
Comp Plan Design (Have they designed and implemented effective structures?)
Tech Chops (Especially important in today’s AI-driven market, product-led, and complex, ever-changing sales orgs)
Industry Knowledge (Important if your customers expect deep credibility)
Go-to-Market Model Experience (SMB, MM, ENT, inbound, outbound, channel, PLG, Customer-Led, etc.)

What matters most depends on:

Stage – are you still validating or scaling?
Motion – inbound? Outbound? Product-led? Partner-led?
Complexity – how technical is the sale? How long is the cycle? How many buyers are involved? How is the market changing?

Remember that scorecards only help when you know what you are looking for – ground every scorecard item in observable, testable signals, not intuition. If you are not confident in what to include, how to prioritize it, or how to assess it in an interview, get help. Your scorecard sets the foundation for how you hire, evaluate, and ultimately hold this person accountable.

What third-party services and tools are available to help recruit sales leaders?

If you don’t have the experience, network, or bandwidth to run a rigorous process, consider using third-party support – it can save time, protect your brand, and increase your chances of getting your hire right the first time. The right third-party service depends on your business situation and People needs.

Types of Recruiters
Type	What They Do	Benefits	Risks
Internal Recruiters	A member of your People team who manages hiring across functions	Helpful for repeatable roles or hiring leverage across departments	• Often stretched thin and may lack the functional depth to vet sales leaders effectively • Risk of long timelines and surface-level assessments
Generalist Executive Recruiters	External partners who recruit across multiple functions (Sales, Product, Marketing, etc.)	Can support a range of leadership hires and build long-term understanding of your company	• May not have deep expertise in evaluating sales leaders • If not exclusive, you risk being deprioritized in favor of faster-moving clients
Specialist Recruiters (e.g., Sales)	External partners focused exclusively on sales leadership recruiting	Deep functional networks and faster, more targeted vetting. Likely to shorten time-to-hire and raise the bar on quality	• Higher cost • If the firm delegates to junior team members or lacks true search expertise, you may not get full value →confirm who is actually doing the work
Larger Executive Search Firms	Well-known global firms with high-end retained search offerings	Can bring prestige and access to candidates in upper enterprise or public company spaces	• Often have minimum compensation thresholds (around $300K+), fees starting around $100K, and may ask for equity • Better suited for later-stage companies with enterprise-level hiring needs

Recruitment Firm Engagement Models
Model	How It Works	When to Use It	Watchouts
Contingent Search	You can work with multiple firms and only pay if you hire their candidate	If you want speed, low upfront cost, and already have internal hiring coverage	• Often transactional • Quality varies widely → your brand may be poorly represented if firms are racing each other, and candidates can feel burned • Fees typically range from 20-30%of base comp
Blended Contingent + Upfront Model	A hybrid where you pay a small amount up front to secure focus and better candidate experience, with the rest contingent on hire	When you want to improve attention and accountability without fully committing to a retained model	• Can still be inconsistent if expectations and ownership are not clearly defined → ensure clarity around deliverables and time commitment
Retained Search	Exclusive partnership where the recruiter owns and runs the full process	Ideal for executive-level roles where quality, alignment, and confidentiality matter	• Costs more (typically 30-35 % of total comp), but delivers a true partner in the process • Make sure the firm brings rigor, functional depth, and is not outsourcing the work internally

The best tools that you use in sales can be used for recruiting – sales and recruiting are not dissimilar. Anything you use for sales research and outreach, like LinkedIn, can be repurposed for researching and contacting candidates. Recruiting is a GTM motion, and many of the same strategies and tools apply. What matters most is using them with intention and structure.

Source	Use Case
LinkedIn (free or paid)	Core platform for sourcing, research, and outreach. Also helpful for seeing common connections or patterns in past experience
Slack Communities	Startup and operator communities can surface strong referrals and open up conversations with experienced leaders who are not actively applying
Events and Conferences	Sales-focused events like SaaStr, Pavilion, or industry-specific gatherings are ideal for live interaction and off-the-record conversations
Podcasts	A great place to observe how someone thinks and communicates. Also a signal for credibility, influence, and functional relevance
Your Current Team	Your employees should be your biggest megaphone. They know what great looks like and can help amplify your search or make warm intros
Rejected Candidates and Runners-Up	Candidates who didn’t make the cut in previous searches but showed promise may now be the right fit. Timing and scope evolve, so should your pipeline strategy

Recruiting Tips:

Great hiring is about timing and context more than anything else – keep your pipeline warm and revisit strong candidates regularly.
Hiring a sales leader is not a volume game – it is about clarity, consistency, a proven system to reduce the margin for error, and using the right support when it matters.
Functional depth is critical – lean into the right partner who brings the functional depth and experience to match the stakes. The earlier into the process you involve this partner, the better.

What messaging works well in attracting great sales leaders?

Top sales leaders are not sitting around waiting to be found. They are busy building, leading, selling, and scaling. And they have no shortage of opportunities that come their way. If you want to reach them, your message has to stand out… fast.

Whether it is a job description or cold outreach, the same rule applies: Be clear, be relevant, and speak to them, not just the checklist or pitching a role like everyone else.

Medium	Messaging Tips	Example
Outreach	Make it personal, clear, and tied to value – get to the point and show that you’ve done your homework. Connect the dots between their experience and what your company needs right now. Demonstrate that: You’re paying attention You value how they think, not just what they’ve done You’re building something worth their time You’ve done the work to earn their time	“You just shared a post about scorecards and how you think about the five core evaluation categories as a sales leader. That’s exactly how we’re thinking about the sales org we’re building. I’d welcome the chance to learn more about how you’re using yours and compare notes.”
Job description	Think of a job description as an invitation to a deeper conversation – it shouldn’t tell the entire story or read like a laundry list of vague traits and jargon. Be clear and unique – don’t copy and paste job descriptions from other companies. Applications are a two-way street; when you lead with clarity about the work, the right people will lean in. When you lead with fluff, jargon, or generalizations, you either attract the wrong profiles, waste priceless time, or get ignored entirely.	A good job description includes: • The problems this person will be solving • What success looks like in the first 6-12 months • The kinds of decisions they will own • The outsized impact they can have on the business • The kind of environment they will step into
In general	Use inclusive, signal-driven language – if you want to attract a more diverse and balanced pool of candidates, you need to start by checking your language. Sales job descriptions often lean aggressive, competitive, or overly masculine, which can unintentionally repeal great candidates who are more collaborative, strategic, or customer-centric. Note: inclusive language doesn’t “water down” your job description. It increases your chances of reaching exceptional candidates who may not look like the last 5 people you hired.	Run your job descriptions through a tool like Textio, which helps remove gender-biased and exclusionary language and encourages clearer, more inclusive writing.

What should Sales leader compensation packages include?

With sales comp, you get what you pay for – excellent leadership is expensive. Don’t expect to find a discount on someone who knows how to build a high-performing through change and ambiguity while carrying the weight of growth and scale.

Sales leader compensation can be influenced by multiple levers – there are over 30 comp levers beyond base, variable, and equity. While signing bonuses, guarantees, and vesting triggers can make a comp package more compelling, the key components should include:

Base plus variable comp – 50/50 to 70/30 split is typical depending on role and stage
Meaningful equity – a key lever for early and growth-stage companies
Accelerators – performance-based incentives for exceeding targets (win/win)
Executive coaching or training budget – most great leaders want continued development
Benefits – a comprehensive benefits package that reflects company maturity and supports health, wellness, and overall employee well-being

The right comp package supports business goals – your comp strategy should reward the outcomes and behaviors that matter most to the company based on its current stage. If the structure is misaligned, even a generous package will miss the mark.

Note: as AI continues to evolve, the role, reach, and compensation philosophy of sales leaders will shift – expectations around strategy, competency, inputs, output, capacity, support needs, and even how compensation is structured will adjust as AI matures. The key is staying grounded in what the business needs now, the jobs to be done, and keeping an eye on where things are headed.

Who should be involved in hiring sales leaders?

The founder or CEO – the person sales will report to must be deeply involved. This hire is not a box to check or a final-round meet-and-greet. Your sales leader will be your strategic partner, driver of revenue, an extension of your voice in the market, a representative of your business to your customers and board, and a reflection of your leadership. Culture fit, communication style, and alignment start with you.

Co-founders – even if sales will not report directly to them, your co-founders should have a voice in the process. They have helped shape the business and culture, and they will be working closely with this person. Alignment between active co-founders is critical, especially for high-impact executive hires.

Cross-functional leaders – sales does not work in a vacuum. The earlier you involve these stakeholders, the faster your new hire can build trust, understand dependencies, and start making an impact. Include the leaders this person will rely on to succeed:

Marketing: for pipeline, messaging, and campaign alignment
Customer Success: for handoffs, retention, and expansion strategy
Product: for customer feedback, roadmap inputs, and cross-team priorities
RevOps: for process, metrics, systems, and accountability
Finance: for forecasting, resource planning, and GTM efficiency

Active board members – if your sales leader will be presenting in the boardroom, key board members should have a seat at the hiring table. Sales is a core part of your revenue ecosystem, and board alignment matters. However, be thoughtful about which board members to involve and whether they appreciate the realities of operating vs. investing.

Note: everyone involved in the hiring process should know how to interview – this is not the time to figure out what good looks like or how to assess it. The wrong person in the room can confuse, derail, or misrepresent what matters most. If someone lacks the experience, structure, or confidence to effectively evaluate candidates, get them the support they need or remove them from the process.

What can you do to help close a sales leader candidate you really like?

Focus on mutual alignment, no persuasion – great sales leaders don’t need to be sold. They need clarity, transparency, and the opportunity to solve meaningful problems with people they trust.

To convey mutual alignment:

Be honest about the good, bad, and real – tell them what it’s actually like to work with you. What do the best days look like? What about the hardest? What’s messy, what’s working, and what’s still in motion? If you’re aligned, you won’t have to convince them; they’ll want in.
Don’t fall into the trap of “selling the role” – too many recruiters and hiring managers think their job is to win over the candidate. That’s how mis-hires happen. Skip the hype and get into the actual work. Your goal is a shared reality, not a rehearsed pitch.
Watch how they respond to the real problems – talk openly about what’s not working.
If their energy shifts, they lean in, and you hear “this is the kind of challenge I like,” that’s a sign you’ve got a fit. If they hesitate, avoid specifics, or brush over what needs fixing, they’re probably not the one.
Involve the right people at the right time – let them meet key cross-functional partners, future team members, and board stakeholders. Give them access to the environment they’d actually be working in. You’re not selling, you’re building trust.

Overall

What are the most important pieces to get right?

Clarity and alignment are key – they are the foundation of a successful hire. Everything else builds from there.

Match the hire to the actual work – know what phase you’re in and what outcomes this person will own. Your needs at $1M ARR are wildly different from your needs at $20M. Find someone whose track record maps to the jobs to be done now, not three phases from now.

Validate what they’ve actually done – social media profiles tell stories. Your job is to find the truth. Ask how they approached a situation, what they built, how they led, and what broke under their watch. Have them walk you through the specifics. Push past the talking points to uncover real experience, real depth, and real alignment.

Build a process that reflects your expectations – a sloppy process tells a strong candidate that your company is not ready. The way you run interviews is the first signal of how you operate. Make it count.

What are common pitfalls?

These are the traps that derail sales leadership hiring, and they’re more common than most founders realize.

Hiring a player-coach – it sounds efficient, but building the sales foundation and managing a team are two different full-time jobs. Eventually, something breaks, and it’s usually trust, performance, or both. The built-in conflict (i.e., asking someone to compete for deals while managing the comp plan, territory design, and pipeline review) is not sustainable or fair to the team.

Assuming that all sales leaders are interchangeable – there is no such thing as a generic “great sales leader.” There are builders, scalers, fixers, and maintainers, and what worked at one company or stage won’t always translate. If you can’t clearly articulate what kind of leader you need and why, you’re not ready to make the hire. And if you hire based on logos or personality alone, don’t be surprised when it doesn’t work.

Taking candidate statements at face value – “I doubled revenue.” “I built the team from scratch.” “I owned GTM.” These sound great, but without context, they’re meaningless. You need to validate:

What exactly did they own?
What stage and segment were they working in?
Who else was involved?
What broke and how did they respond?

Falling for the shiny object – this could be a big-name logo, a flashy title, or a killer interview. None of these are proof that someone can do the job you need done right now.

Hiring Sales Leaders