Hiring Your First GTM Team: 10 Costly Mistakes Founders Make and How to Avoid Them

You’ve found early traction. Customers are biting. Growth feels… within reach. But one thing’s clear: you can’t keep doing it all yourself.

Welcome to the most thrilling — and dangerous — phase of startup growth: hiring your first go-to-market (GTM) team. It sounds simple. Bring in a seller, a marketer, or both. Scale what’s working. But the truth? Most founders mess this up. Badly.

Below are the hard truths, overlooked lessons, and real-deal insights you won’t find in your typical “hire a Head of Sales” blog post. If you're a founder, first-time sales leader, or newly minted Head of Growth — read on.

1. Build a Simple Sales Method Before You Hire

If your sales “strategy” is just winging it on every call, your first hire is walking into chaos.

You don’t need a Salesforce certification or a 50-page playbook. But you do need clarity:

• Who are your ideal customers?

• What are their 3 biggest objections?

• What closes deals? What kills them?

Why this matters:

Without this structure, your new hire spends their first month flailing — not selling. Even the best AE can’t scale a system that doesn’t exist. A framework like MEDDPICC or SPICED (or a DIY version) helps them sell like you, faster.

When working with TruckX, we discovered their team was struggling because each sales rep had their own approach. By implementing a standardized sales methodology, we helped them scale from $2M to $16M ARR in just 18 months. Structure breeds success!

Expansion tip: Before writing that job description, spend two weeks documenting:

• Your current sales process (even if it's just founder calls)

• The last 10 deals you won (and why)

• The last 5 deals you lost (and why)

This becomes your new hire's playbook. It's also how you'll know if they're adding value or just adding headcount.

2. Quotas That Demoralize Will Kill Momentum

Early-stage founders often slap on a sales quota like: “$500K ARR in 90 days.” Based on what? Vibes?

Instead, start here:

• What’s your average deal size?

• What’s your current conversion rate?

• How long does it take to close a deal?

Then build quotas rooted in reality, not investor pressure.

Why this matters:

When a new hire sees an impossible target, they check out. Or worse — they churn. Early wins matter more than big wins. Build confidence, then compound.

Working with a Series B financial services startup, we noticed their sales team was drowning under unrealistic quotas. After realigning expectations with achievable yet challenging goals, team morale skyrocketed, and they finally achieved product-market fit.

Pro tip: Set a "confidence quota" for the first 90 days. It should be lower than what you ultimately need but high enough to validate potential. Then scale up gradually as your new hire builds momentum.

3. Don't Hire a Sales Leader Before PMF

Many founders fall into the trap of hiring a senior VP of Sales… to figure out the sales motion.

Big mistake.

If you haven’t sold the product yourself — repeatedly — you don’t have product-market fit. And no, one lucky enterprise pilot doesn’t count.

Why this matters:

Hiring a leader before PMF leads to strategy theater. They’ll bring playbooks from mature orgs that don’t fit your messy, pre-PMF world. Hire doers, not decorators.

4. Culture > Credentials

You don’t need someone who scaled a $100M sales org. You need someone who’s scrappy, curious, and hungry.

Someone who loves uncertainty. Someone who asks:

“What can I build?” — not, “What do I get to manage?”

Why this matters:

Culture misalignment kills morale faster than missed numbers. Early-stage startups need energy, not ego.

At Phi, we've repeatedly seen how building customer success into your startup's DNA creates a culture where your GTM team naturally aligns with your vision. When working with DataTruck, we specifically hired for cultural alignment rather than just experience, which helped us scale them to $1M ARR and reduce CAC by 97%.

Founder exercise: Before interviews, list your company's 3 non-negotiable values. Then craft behavioral questions that reveal whether candidates truly embody them. For example, if "resourcefulness" is a value, ask about a time when they had to sell without resources or support.

5. One Role ≠ Five Roles

“I want someone who can sell, do marketing, manage CS, write content, and run ops.”

Cool. So… a unicorn?

Nope. You’ll just burn out a smart hire.

Do this instead:

• Prioritize the most urgent GTM gap (e.g., converting inbound? Outbound? Retention?)

• Hire specifically for that

• Fill other gaps with contractors, advisors, or founder hustle

Why this matters:

Clarity wins. A focused hire delivers results. A scattered hire delivers excuses.

6. Scorecards Beat Gut Feel (Especially When You're Rushed)

Yes, you’re busy. Yes, you’re drowning. But if you rush this hire without structure, you’ll regret it.

Use a scorecard. Rank each candidate across 4–5 qualities that matter (e.g., founder-stage experience, grit, coachability). Run a test project or a mock call.

Why this matters:

Speed + structure = smart hiring. Top candidates won’t wait. But you can’t afford to get this wrong.

7. Co-Sell Before You Let Go

Founders often make two mistakes after the first GTM hire:

1. Micromanage every call

2. Disappear completely

Here’s the better path: co-sell the first 20 deals together.

Let them shadow you. Then flip it. You shadow them. Debrief. Improve. Repeat.

Why this matters:

It’s not just sales knowledge they need — it’s your conviction. When customers hear it from the founder and the AE, trust builds faster.

One of our most successful implementation strategies has been establishing multi-threaded customer relationships from the beginning. At AtoB, we helped them create a co-selling process that catapulted them to an $800 million valuation by ensuring knowledge transfer happened organically while maintaining founder-level conviction.

Structured approach:

• Weeks 1-2: New hire observes 100% of calls

• Weeks 3-4: New hire leads parts of calls (intro, discovery, specific objection handling)

• Weeks 5-8: New hire leads full calls with founder observing

• Weeks 9+: Independent calls with weekly role-play sessions

8. Advisors and Fractional Hires Are Underrated

You don’t need to go all-in on full-time hires.

Got budget constraints? Bring in a fractional GTM leader to build the system. Need an expert eye? Have an investor or advisor join interviews.

Why this matters:

Fractional and advisory talent fills gaps without bloating burn. It’s smart leverage while you scale intentionally.

9. Align Incentives — and Set Expectations Early

A comp plan is more than base + OTE. It’s a signal.

Offer equity if you can. Explain how performance is measured. Share what support will and won’t exist. Spell it all out in week one.

Why this matters:

Surprises kill trust. And trust is what keeps early hires around when things get hard (which they will).

10. Don’t Just “Hire in Order.” Solve Bottlenecks

Conventional wisdom says:

Sales → Marketing → CS → RevOps

Reality?

It depends.

If your first hire is closing deals but struggling with handoffs, maybe your next hire is a Customer Success lead. If pipeline dries up, hire demand gen next.

Why this matters:

Growth bottlenecks are dynamic. Solve them as they emerge. Don’t follow someone else’s blueprint — build your own.

BONUS: Remote GTM Teams Can Work — But They Need Extra Structure 

With distributed teams becoming the norm, building remote GTM functions requires special consideration.

Keys to success:

• Over-document everything (calls, processes, customer feedback)

• Schedule regular synchronization meetings (not just check-ins)

• Create clear decision-making frameworks

• Build intentional cultural touchpoints

Using effective remote team management strategies, we helped one client build a high-performing GTM team across three time zones, resulting in 40% faster growth than their previous co-located team.

Ready to Build Your GTM Muscle Without the Hiring Headache? ⚡

If you're at the edge of scaling but unsure whether to hire a full GTM team just yet — there's a better way.

As the GTM landscape evolves in 2025, more founders are discovering the power of AI-enhanced GTM strategies and fractional expertise.

Phi Consulting partners with startups to launch fully-managed GTM pods — sales, marketing, and RevOps teams built for execution, not just strategy.

✅ Pre-trained in startup sales✅ Ramp in days, not months✅ Aligned on results (not just activity)

Our approach combines the 8 key components of winning B2B GTM strategies with execution teams that have already worked together, eliminating the costly trial-and-error of building your own team from scratch.

We've helped companies like Motive, DigitalOcean, Shipwell, and TruckX accelerate revenue without bloating headcount.

👉 Book a free GTM strategy call to see if Phi's pods can help you skip the hiring maze — and start closing faster.

Remember: Your first GTM hires will shape your company's growth trajectory for years. Take the time to get it right — or partner with experts who've done it before. Your runway (and your future self) will thank you.