For two years, I was the only product marketer at a 120-person B2B SaaS company. I owned everything: launches, competitive intel, sales enablement, customer research, messaging, positioning.
I was drowning. Working 60-hour weeks. Missing deadlines. Disappointing stakeholders. The VP Marketing finally approved headcount for two more PMMs.
I thought adding two people would make everything three times easier. We'd split the work, move faster, ship better quality.
I was naive.
Going from solo PMM to a team of three didn't make things three times easier—it made them temporarily harder. Suddenly I was managing people while still doing my own work. I had to delegate tasks I'd always owned. I had to build processes that didn't exist. I had to align three people instead of just executing myself.
Six months later, we'd figured it out. The team was delivering more and better work than I ever could alone. But that first six months was brutal—and nobody had warned me about what actually changes when you scale from one to three.
Here's what I learned about the transition from solo PMM to small team, and what I wish I'd known before we started.
What I Expected vs. What Actually Happened
What I expected: We'd split the existing workload three ways. I'd do launches, Person A would do competitive intel, Person B would do sales enablement. Clean division of labor.
What actually happened: The work didn't split cleanly. Launches required competitive intel. Sales enablement required launch knowledge. Customer research informed everything. We spent the first month duplicating work because we hadn't figured out collaboration yet.
What I expected: Two experienced PMMs would hit the ground running. Minimal training needed.
What actually happened: Even experienced PMMs need context on our specific market, product, customers, stakeholders, and company culture. Onboarding took 6-8 weeks minimum.
What I expected: More people = more output immediately.
What actually happened: Output actually dropped in Month 1-2 while I onboarded the team, built processes, and figured out how to delegate. We recovered to baseline by Month 3 and exceeded my solo output by Month 4-5.
What I expected: I'd finally have time for strategic work.
What actually happened: I spent 50% of my time managing for the first three months. Strategic work didn't increase until Month 5 when the team was truly self-sufficient.
The transition was harder than I expected but worth it. But I would have managed expectations better if I'd known what was coming.
The First Decision That Shaped Everything: How to Divide Work
The biggest early decision: How do we split responsibilities?
Option 1: Specialization (each person owns a function)
- Person A: All launches
- Person B: All competitive intel
- Person C: All sales enablement
Option 2: Generalization (everyone does everything)
- All three PMMs work on launches, competitive work, and enablement
- Projects assigned based on capacity, not specialty
Option 3: Product-based (each person owns product lines)
- Person A: Product Suite 1
- Person B: Product Suite 2
- Person C: Product Suite 3 + new releases
I started with Option 1 (specialization) because it seemed cleanest. It failed within three weeks.
Why specialization failed:
Our launches weren't big enough to keep one person busy full-time. The "launch PMM" would have two launches one month, zero the next month. Uneven workload.
Meanwhile, competitive intel was steady-state work but didn't fill 40 hours per week. The "competitive PMM" ran out of work by Wednesday.
Sales enablement was reactive and spiky. Sometimes we'd have major training needs, sometimes nothing for weeks.
Functional specialization created feast-or-famine workloads. Some weeks people were overwhelmed, other weeks bored.
What actually worked: Hybrid model
We switched to a hybrid approach:
Core ownership areas (60% of time):
- Each PMM had a primary focus area where they built deep expertise
- Person A: Launch management and coordination
- Person B: Competitive intelligence and win/loss
- Person C: Sales enablement and customer research
Shared work (40% of time):
- Everyone contributed to launches (not just the launch PMM)
- Everyone created competitive content (not just the competitive PMM)
- Everyone supported sales (not just the enablement PMM)
How this worked:
For a major launch:
- Launch PMM led planning, timelines, cross-functional coordination
- Competitive PMM contributed competitor positioning and battle cards
- Enablement PMM created training materials and sales certification
- All three collaborated on messaging
This balanced workloads while still building specialized expertise.
The Process That Didn't Exist (Until We Built It)
As a solo PMM, I had no formal processes. I just did the work.
- Launch planning? I'd sketch out a timeline in Google Docs.
- Competitive intel? I'd update battle cards whenever I noticed competitor changes.
- Sales enablement? I'd create materials when Sales asked for them.
Informal, ad-hoc, reactive. It worked for one person because everything lived in my head.
With three people, informal processes broke immediately.
Week 2 disaster:
Person A asked: "How do we decide launch tiers?"
Me: "Well, it depends on the feature size and target audience..."
Person A: "Is there a framework?"
Me: "Not written down. I just kind of know based on experience."
Person B asked: "Where do we store competitive intel?"
Me: "Some is in Notion, some in Google Drive, some in old Slack messages..."
Person B: "What's the source of truth?"
Me: "Uh..."
Person C asked: "What's the process for creating battle cards?"
Me: "I just... create them when needed?"
Person C: "How often should they be updated?"
Me: "When competitors change?"
Person C: "Who monitors competitors?"
Me: "I guess I did..."
Every question revealed a gap in documented process. What I'd done intuitively as a solo PMM needed to be explicit as a team.
The processes we had to build:
Week 3-4: Launch framework
- Launch tier definitions (T1/T2/T3)
- Standard timelines for each tier
- Launch brief template
- Stakeholder approval process
- Launch checklist by tier
Week 5-6: Competitive intelligence workflow
- What competitors to monitor actively
- Weekly competitive intel update cadence
- Battle card ownership and refresh schedule
- Win/loss interview process
Week 7-8: Sales enablement standards
- Enablement deliverable templates (one-pagers, FAQs, decks)
- Training delivery process
- Sales certification requirements
- Feedback collection mechanism
Building these processes was painful. It felt like we were moving slower to move faster later. But by Month 3, the investment paid off. New team members could execute without asking me how to do everything.
The Meetings That Suddenly Mattered
Solo PMM schedule: Work whenever, however. No recurring meetings except stakeholder 1:1s.
Team of three: Suddenly we needed coordination meetings or we'd be duplicating work and stepping on each other.
The meeting structure we landed on:
Monday Team Standup (30 min):
- What each person is working on this week
- Dependencies and collaboration needs
- Blockers and questions
This prevented three people from unknowingly working on the same thing.
Wednesday Mid-Week Check (15 min):
- Quick pulse on progress
- Adjust priorities if needed
- Flag emerging issues
This caught problems before they became disasters.
Friday Team Review (45 min):
- Share work completed this week
- Collective feedback and learning
- Plan next week priorities
This ensured knowledge sharing and quality control.
Monthly Retrospective (60 min):
- What's working, what's not
- Process improvements
- Skill development needs
This drove continuous improvement.
Total meeting time: 2.5 hours per week
This felt like a lot compared to my solo schedule. But the alternative was three people working in silos, duplicating effort, and misaligning with stakeholders.
The meetings weren't overhead—they were coordination infrastructure that prevented waste.
The Skills Gaps We Discovered
As a solo PMM, I knew my skill gaps but worked around them.
Weak at data analysis? I'd partner with Product Analytics for insights. Weak at design? I'd use Canva templates and keep things simple. Weak at technical positioning? I'd lean on Product team for help.
With a team of three, skill gaps became more visible and more problematic.
Month 2 realization:
Person A was great at strategic messaging but weak at project management. Launches missed deadlines because tasks weren't tracked systematically.
Person B was excellent at competitive analysis but struggled with sales enablement. Battle cards were thorough but sales reps found them too complex.
Person C was strong on execution but lacked strategic thinking. Enablement materials were delivered on time but didn't connect to broader positioning.
Together, we covered more ground than I could solo. But we also exposed gaps that needed addressing.
The skill development plan we built:
Individual development:
- Each person identified 1-2 skill gaps to develop
- Quarterly learning goals with specific outcomes
- Budget for courses, conferences, or coaching
Team cross-training:
- Monthly "skill share" where one person taught something they knew
- Shadowing on projects outside your core area
- Peer review on major deliverables
Hiring for gaps:
- When we eventually got headcount for PMM #4, we hired specifically for skills the team lacked (technical product marketing expertise)
The Decision-Making That Needed Clarity
Solo PMM decision-making was simple: I decided everything within PMM's scope.
Team decision-making required structure or we'd have analysis paralysis.
The framework we established:
Level 1: Individual decisions (no approval needed)
- Minor updates to existing materials
- Day-to-day execution within agreed plans
- Small tactical adjustments
Example: Updating a battle card with new competitor features.
Level 2: Team decisions (discuss with team first)
- New processes or frameworks
- Significant changes to existing programs
- Resource allocation and prioritization
Example: Changing how we structure launch tiers.
Level 3: Leadership decisions (needs my approval)
- Budget requests over $5K
- Headcount or organizational changes
- Commitments to executive stakeholders
Example: Proposing a new competitive intelligence platform.
Level 4: Cross-functional decisions (needs VP/executive input)
- Changes affecting other teams
- Strategic positioning shifts
- Major program launches
Example: Recommending change to company messaging architecture.
This framework eliminated the "do I need approval for this?" question that was slowing us down.
What Got Better (And What Got Worse)
What improved dramatically:
Quality of work: Three brains produced better thinking than one. Peer review caught gaps I would have missed.
Coverage: We could finally be proactive instead of reactive. Customer research that I never had time for as a solo PMM became regular practice.
Stakeholder relationships: Three people built broader networks across Product, Sales, and Marketing than I could alone.
Continuity: Someone could cover when I was out. As a solo PMM, my vacation meant PMM work stopped.
What got worse (temporarily):
Speed on small tasks: Things that I'd ship in 30 minutes as a solo PMM now took coordination. "I need a quick one-pager" became "Let me check with the team on messaging and timeline."
Consistency: Three people meant three styles. Our early battle cards looked different depending on who created them. We had to build templates and style guides.
Decision speed: Solo PMM meant I could pivot immediately. Team of three meant I had to align three people before changing direction.
My time for hands-on work: I went from 90% execution to 50% execution / 50% management. This was the right trade-off long-term but felt frustrating early on.
The Unexpected Management Challenge
I'd never managed people before. I thought it would be straightforward: Assign work, review output, provide feedback.
It wasn't.
Challenge 1: Different work styles
Person A wanted detailed briefs and clear expectations upfront. Person B preferred high-level direction and autonomy to figure out the approach. Person C needed frequent check-ins and validation.
I had to manage three people three different ways.
Challenge 2: Uneven performance
Person B was a rockstar from day one. Delivering high-quality work independently.
Person A took 8 weeks to ramp and initially needed significant guidance.
Person C was strong on execution but struggled with ambiguity.
I had to calibrate my involvement to each person's needs while not showing obvious favoritism.
Challenge 3: Interpersonal dynamics
Person A and Person B had different philosophies on how competitive intel should work. Their disagreements created tension.
I had to mediate, establish norms, and sometimes make judgment calls that disappointed one person.
What helped:
Weekly 1:1s: 30 minutes per person to discuss work, provide feedback, address concerns.
Clear feedback loops: Don't wait for quarterly reviews. Give real-time feedback on what's working and what's not.
Team norms: Explicitly discuss how we work together, make decisions, and handle disagreements.
Defaulting to documentation: When the same question came up twice, we documented the answer.
For Teams Scaling PMM Operations
As PMM teams grow from one to three people, operational complexity increases dramatically. Many teams find value in consolidated platforms that can support multiple PMMs working across competitive intelligence, launches, and enablement without fragmenting workflows across disconnected tools. Solutions like Segment8 demonstrate how integrated approaches can maintain team alignment and workflow consistency as headcount scales—reducing the coordination overhead that often bogs down newly-formed PMM teams.
The Timeline Nobody Warns You About
Month 1: Slower than solo
- Training new team members
- Building processes that didn't exist
- Figuring out collaboration patterns
- Output: 70% of solo PMM output
Month 2-3: Back to baseline
- Team starting to work independently
- Processes in place but still iterating
- Some coordination inefficiencies
- Output: 100% of solo PMM output
Month 4-5: Starting to scale
- Team hitting stride
- Clear roles and workflows
- Quality improving
- Output: 150-200% of solo PMM output
Month 6+: True scale
- Team self-sufficient
- Proactive instead of reactive
- Building programs, not just executing tasks
- Output: 250-300% of solo PMM output
The mistake I made: Expecting immediate 3x output. The reality: 6 months to achieve meaningful scale.
If I'd known this, I would have:
- Planned for a ramp period instead of expecting immediate productivity
- Invested more heavily in onboarding and process documentation upfront
- Set stakeholder expectations about the transition timeline
The Uncomfortable Truth About Scaling PMM
Going from solo PMM to a team doesn't immediately solve your problems—it trades one set of challenges for another.
Solo PMM challenges:
- Doing too much work
- No time for strategic thinking
- No backup when you're out
- Limited expertise breadth
Team of three challenges:
- Coordinating multiple people
- Building processes that didn't exist
- Managing different work styles
- Maintaining consistency
- Learning to delegate instead of doing
The transition period is genuinely hard. You're doing your old job (execution) plus a new job (management) simultaneously. You'll feel less productive for months.
But the payoff is real. Six months in, our PMM team was delivering work I could never have produced alone. We were proactive instead of reactive. We were building programs instead of just responding to requests. We had coverage, redundancy, and diverse expertise.
The question isn't whether scaling is worth it—it is. The question is whether you're prepared for the transition period where things get harder before they get better.
Most people aren't warned about this. I'm warning you.
If you're scaling from solo to team:
Expect 3-6 months of transition pain. Plan for it. Build processes early. Invest in onboarding. Learn to delegate even when it feels inefficient. Accept that you'll manage more and execute less.
The team will eventually become a force multiplier. But first, it's an investment that requires patience, structure, and a tolerance for the messy middle where you're rebuilding how PMM works while still delivering on existing commitments.
It's worth it. But it's harder than you think.