I was finally getting my first PMM hire. After two years as a solo product marketer doing everything—launches, competitive intel, sales enablement, customer research, messaging—I was burned out and lobbying hard for headcount.
The CFO approved one role. Just one. This hire would determine whether PMM scaled successfully or stayed a bottleneck. No pressure.
I thought I knew exactly what I needed: a senior PMM who could own launches end-to-end while I focused on strategy. Someone with 5+ years of experience who'd done this before and could hit the ground running.
I was wrong about almost everything.
Six months after that hire started, I realized I'd optimized for the wrong things. I hired for experience when I should have hired for adaptability. I looked for someone who'd worked at similar companies when I should have looked for someone who thrived in ambiguity. I prioritized technical skills when I should have prioritized cross-functional influence.
That first hire worked out—but only because they were adaptable enough to become what we actually needed instead of what I thought we needed. I got lucky. Most teams aren't so fortunate.
Here's what I learned about hiring your first PMM team member, and what I'd do completely differently today.
What I Got Wrong: Hiring for Experience Over Potential
My job description read like a greatest hits compilation of enterprise PMM requirements:
- 5+ years product marketing experience at B2B SaaS companies
- Proven track record managing product launches at scale
- Experience with competitive intelligence programs
- Strong stakeholder management across Product, Sales, and Marketing
- Excellent written and verbal communication skills
The subtext: "I want someone who's already done this job so I don't have to train them."
The problem with hiring this way when you're building a PMM function: the job you think you need done today isn't the job that actually needs doing six months from now.
When you're the solo PMM, you've created systems and workflows that work for a team of one. You've taken shortcuts that don't scale. You've built relationships that are hard to transfer. You've made tradeoffs that new team members will question.
The PMM I hired had run launches at a 500-person company with established processes. We were 80 people with zero processes. She kept asking where the launch checklist template was, who owned messaging approval, what the standard timeline looked like.
There wasn't a template. There wasn't an approval process. The timeline was "whenever we get it done."
She'd learned to operate within structure. I needed someone who could help build structure from chaos.
What I should have optimized for: Someone who'd built PMM programs from scratch, even if at a smaller scale. Someone who'd worked at earlier-stage companies where nothing existed and you had to create it. Someone who thrived when the answer to "how do we do X?" was "I don't know, what do you think?"
Experience matters less than adaptability when you're building a team. A PMM with 3 years at startups who's worn every hat will often outperform a PMM with 7 years at enterprises who's only owned one workflow.
What I Got Wrong: Hiring for Skills Instead of Gaps
I made a list of everything PMM needed to do, then hired someone who could do all of it.
Launches. Competitive intel. Sales enablement. Messaging. Customer research. Pricing support. Analyst relations.
The problem: I could already do all those things. I was hiring someone to replicate me, not complement me.
Three months in, I realized we were duplicating work instead of dividing it. We both worked on launches. We both did competitive research. We both created enablement materials. Instead of 1x capacity becoming 2x capacity, we'd gone from 1x to maybe 1.4x.
We were both good at the same things and both weak at the same things. When Product asked for technical documentation support, neither of us had deep developer marketing experience. When Sales asked for vertical-specific messaging, neither of us had industry expertise.
What I should have done: Hired for my gaps, not my strengths.
I was strong on strategy, messaging, and cross-functional influence. I was weak on execution, project management, and analytical rigor.
I should have hired someone detail-oriented who loved process, could manage launch timelines without me, and got excited about building dashboards to track metrics. Someone who complemented my weaknesses instead of mirroring my strengths.
When you hire your first team member, resist the urge to hire someone just like you. Hire someone who makes the team better by being different.
What I Got Wrong: Optimizing for "Hit the Ground Running"
I wanted someone who could start making an impact on day one. No ramp time. No training period. Just immediate productivity.
So I hired someone from our industry who understood the product category, knew the competitive landscape, and could speak the technical language.
The unintended consequence: they had very strong opinions about how PMM should work based on their previous company. And those opinions often conflicted with how we'd been operating.
"At my last company, we always did launch tiers this way." "The messaging framework I used before worked really well." "We should be using this competitive intel tool—it's what everyone uses."
Sometimes they were right and I needed to change. Sometimes our context was different and their approach wouldn't work. Either way, every decision became a negotiation about whose way was better instead of collaborative problem-solving.
What I should have optimized for: Someone smart and adaptable who could learn our context quickly, even if they didn't know the space deeply on day one.
A PMM who'd done great work in a different industry can often ramp faster than you expect—and brings fresh perspectives that prevent groupthink. They ask "why do we do it this way?" about things you've stopped questioning.
The best first hire I ever made (in a later role) came from fintech and we were in dev tools. She spent two weeks asking what felt like basic questions, then completely redesigned our customer segmentation because she saw patterns we'd missed. Her outsider perspective was more valuable than domain expertise would have been.
What I Got Wrong: Hiring for Today's Needs, Not Tomorrow's
When I wrote the job description, I focused entirely on my current pain points:
"We need help with product launches. I'm doing 6-8 per quarter and drowning."
So I hired someone great at managing launches. Problem solved, right?
Wrong.
Three months after they started, the company pivoted strategy. Instead of lots of small feature launches, we were doing two major releases per year with bigger bets. The launch volume problem disappeared.
Suddenly the skills I'd hired for weren't the ones we needed. We needed someone who could run analyst relations programs, build category creation content, and support enterprise sales with industry-specific messaging. All things my hire hadn't done before and wasn't excited about learning.
What I should have done: Hired someone versatile who could grow into whatever the business needed next.
The best PMMs aren't specialists who only do one thing exceptionally well. They're adaptable generalists who can learn new skills as priorities shift. They're comfortable with ambiguity and excited about tackling unfamiliar problems.
When interviewing, I should have asked less about what they'd done before and more about:
- "Tell me about a time you had to do something you'd never done before. How'd you approach it?"
- "What's a skill you taught yourself in the last year?"
- "How do you operate when there's no playbook?"
The answers to those questions predict success better than a track record of similar experience.
What I Got Wrong: Not Testing for Cross-Functional Influence
PMM's superpower is cross-functional influence. You don't have authority over Product, Sales, Marketing, or CS—but you need to influence all of them.
I assessed writing skills, strategic thinking, and launch experience. I forgot to assess the most important skill: the ability to get things done through other people.
My hire was brilliant but struggled to get Product to prioritize her feedback. She'd write detailed positioning docs that sat unread. She'd propose changes to the roadmap presentation and get ignored.
Meanwhile, I'd have a 15-minute conversation with the VP Product and he'd immediately update his messaging. Same feedback, different outcome.
The difference wasn't quality of ideas—it was influence and relationship building. I'd spent two years earning trust and understanding how to frame suggestions in ways that resonated. She hadn't.
What I should have tested for: Actual evidence of cross-functional influence.
In interviews, I should have asked:
- "Tell me about a time you convinced Product to change their roadmap based on market insights."
- "How have you built credibility with Sales teams that initially didn't trust marketing?"
- "Walk me through a situation where you had to influence a decision without authority."
Then I should have checked references specifically on this: "How effective was [candidate] at influencing stakeholders outside their direct team?"
A mediocre writer who can get Product and Sales aligned will have more impact than a brilliant strategist who can't build buy-in.
What I Should Have Prioritized: The Actual Job Description
If I could redo that first hire, here's what the job description would emphasize:
Must-haves:
- Track record of building programs from scratch (not just operating established ones)
- Experience at companies <200 people where you wore multiple hats
- Demonstrated ability to influence cross-functional stakeholders without authority
- Comfort with ambiguity and changing priorities
- Self-directed work style (you won't have a playbook to follow)
Nice-to-haves:
- Product marketing experience (can be taught faster than you think)
- Our industry expertise (fresh perspective often more valuable)
- Specific tool experience (tools change, thinking doesn't)
Interview process changes:
- Work sample: "Here's a launch brief. Build a 30-day launch plan with no template."
- Case study: "Product just changed the roadmap. How do you re-align messaging and enablement?"
- Reference checks focused on adaptability and influence, not just competence
The goal: hire someone who can operate in chaos, build structure where none exists, and get things done through relationships rather than authority.
What Actually Matters in Your First PMM Hire
After making this hire and watching other teams build PMM functions, here's what I now know matters most:
1. Hire someone who complements your weaknesses, not mirrors your strengths
If you're a big-picture strategist, hire a detail-oriented executor. If you're introverted and do your best work in docs, hire someone who builds relationships through conversation. Build a team that's stronger together than either of you alone.
2. Optimize for learning agility over specific experience
The company will change. The strategy will change. The priorities will change. Hire someone who can learn and adapt faster than the business shifts underneath them.
3. Assess cross-functional influence as rigorously as hard skills
Give them a realistic scenario and watch how they'd approach influencing Product or Sales. Check references on this specifically. A PMM who can't build credibility across teams will struggle no matter how skilled they are.
4. Look for people who've built things from scratch
PMM at scale-ups is very different from PMM at enterprises. Someone who's operated in startup chaos will thrive in building your function. Someone who's only worked within established structure will struggle.
5. Hire adults who don't need hand-holding
Your first hire needs to be self-directed. You're still doing your own job plus building the team. You can't micromanage. Hire someone who identifies problems and solves them without being told what to do.
The Interview Questions That Actually Reveal Fit
These questions helped me assess what actually matters:
On adaptability: "Walk me through a time when your company's strategy changed dramatically and invalidated work you'd been doing. How did you handle it?"
Look for: Resilience, ability to pivot without getting defensive, focus on outcomes over attachment to original plans.
On building from scratch: "Tell me about a program or process you built where nothing existed before. What was your approach?"
Look for: Systematic thinking, ability to operate without templates, learning from early failures and iterating.
On cross-functional influence: "Describe a situation where you needed to change a stakeholder's mind when they disagreed with your recommendation. How did you approach it?"
Look for: Empathy for other perspectives, strategic framing, relationship building over time.
On self-direction: "Tell me about a problem you identified and solved without being asked to do it."
Look for: Initiative, ownership mentality, ability to prioritize without direction.
On dealing with ambiguity: "What do you do when you're asked to accomplish something you've never done before and there's no one to teach you?"
Look for: Resourcefulness, comfort with uncertainty, systematic learning approach.
The Reality Check: Sometimes You Hire Wrong and That's Okay
Even with better hiring criteria, sometimes you'll get it wrong. The role will evolve in unexpected ways. The person won't adapt like you hoped. The team dynamic won't work.
I've made plenty of hiring mistakes since that first one. The difference now is I recognize misalignment faster and address it earlier.
If someone isn't working out:
- Have direct conversations about fit within 90 days
- Be honest about what's not working and whether it's fixable
- Make changes quickly rather than hoping it improves
- Treat people with respect but prioritize the team's success
Your first hire sets the tone for the team culture you're building. Hire well, and you create momentum. Hire poorly, and you spend months recovering.
The Uncomfortable Truth About First Hires
Here's what nobody tells you about hiring your first PMM team member: it will feel harder after they start, not easier.
You go from solo PMM with complete control to manager trying to delegate work you've always done yourself. You go from moving fast alone to moving deliberately as a team. You go from clear accountability to shared responsibility.
For the first 3-6 months, you'll be less productive, not more. You're training someone, building processes, aligning on approach, negotiating decisions. It's an investment that pays off later but feels expensive early.
If you're not prepared for that initial slowdown, you'll get frustrated with your hire when the real issue is the transition.
The teams that scale PMM successfully embrace this reality. They know the first hire is about building foundation, not immediate productivity gains. They invest in onboarding, alignment, and process documentation even though it feels slow.
The teams that struggle try to extract immediate value from their first hire while giving minimal support. Then they're surprised when that hire churns after six months.
Your first PMM hire is a force multiplier—eventually. But first, they're an investment.
What I'd Tell My Past Self
If I could go back and advise myself before making that first hire:
Hire for who you need to become as a team, not who you are today. Hire someone different from you who complements your gaps. Hire for adaptability and influence over experience and credentials. Hire someone who can build in chaos, not just operate in structure.
Test for cross-functional influence as rigorously as strategic thinking. Check references on relationships, not just competence. Ask about times they built from scratch, not just scaled existing programs.
Expect the first six months to be an investment, not immediate ROI. Build onboarding. Document processes. Align on principles. Have patience with the transition.
And when you find someone great who doesn't fit the job description you wrote but fits the job that actually exists—hire them anyway.
The best first hire I never made was a candidate I passed on because they didn't have "enough launch experience." They went to a competitor and built an incredible PMM function. I later hired someone from their team who told me how transformative that first hire had been.
I'd optimized for credentials over potential. I'd missed someone great because they didn't match my checklist.
Don't make my mistake. Hire the person who'll make your team better, even if they don't match what you thought you needed.
For Teams Considering Consolidation
As your PMM team grows beyond that first hire, tool sprawl becomes a real challenge. Many teams find themselves managing disconnected systems for competitive intelligence, launch management, and messaging—creating operational overhead that slows everyone down.
For teams looking to consolidate workflows as they scale, platforms like Segment8 offer integrated approaches that can reduce tool complexity while maintaining functionality across core PMM workstreams. The operational efficiency gains become more valuable as your team grows and coordination costs increase.
That first hire is the foundation. Choose wisely, support thoroughly, and build the team culture you want to scale.