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“The unicorn hire.”

“The jack-of-all-trades.”

“Someone who can flex their left and right brains to drive exponential growth.”

“A rockstar ready to join a mission-driven company with founders value of marketing.”

The Chief Marketing Officer (CMO) or Head of Marketing role is one of the most crucial yet misunderstood positions, especially in a startup. These requirements are designed to be unique but have become a familiar pattern in the tech industry, leading to bad hires and wasted time on both sides.

Founders often hire CMOs expecting miracles, while candidates might need to fully grasp the challenges of building marketing strategies in a high-growth, resource-constrained environment. This mismatch leads to costly missteps, including failed hires, misaligned strategies, and unmet expectations.

Drawing on my experiences as a startup marketing leader and insights from dozens of peers across the industry, I’ll address key misperceptions and mistakes from founders and candidates, along with a roadmap for this vital role right from the start.

Part One: What Founders Get Wrong

1. The Myth of the Instant Fix

Founders often view marketing as a quick remedy for growth problems. Whether they are pressured by the board or feel the role was a missing player in their leadership roster, transitory needs of the business can tend to motivate the need for this hire. They also expect their CMO to solve everything overnight—building brand awareness, driving leads, and boosting customer retention simultaneously.

For example, I was once expected to double the user base in one year. Not only did that incentivize the team to leverage short-term tactics like paid marketing, but this so-called focus also invites long-term issues such as poor retention or a leaky bucket due to attracting the “wrong” audience. This is a classic and all too common example of marketing being expected to overdeliver to solve leaky bucket issues in the product.

The reality is that marketing takes time. To build an effective strategy, proper research is required to identify and understand your target audience. Executing campaigns involves coordinating many cooks in the kitchen, and analyzing results requires patience.

Advice: Founders should approach the marketing function as an investment in long-term growth. Early wins might come from tactical experiments, but sustainable results emerge from a well-aligned strategy.

Ensure your marketing leader has a clear roadmap that balances short-term efforts and a strategy that breaks down levers using a multi-step approach—because one can’t possibly focus on the entire funnel simultaneously with equal effort. Pick the most pressing issue in the funnel for the CMO to focus on (awareness, conversion, retention) or work with them to prioritize ruthlessly. For example, maybe you need to solve activation immediately with experiments but are willing to make a long-term investment to drive the top of the funnel. This is an important discipline that founders need to build, but they often have difficulty clarifying it for their teams.

It might help to align around the ideal 30-60-90 plan during the interview process, along with general expectations in the first year.

2. Misaligned Role Expectations

Founders often don’t understand what type of marketer they need, and marketers don’t always assess the situation they’re getting into (more on this later). This is more common than people realize. I’ve faced it myself firsthand, and many of my peers in the marketing community have confided in me about their own experiences. It’s a classic cliche that has become the elephant in the room. So, let’s talk about it candidly.

Without role clarity, founders risk hiring someone with the wrong skill set, setting both parties up for disappointment. There are key elements to consider:

• Marketing domain expertise: Do they require a brand-builder, a performance and growth marketer, or a product-focused strategist? Most marketers will have progressed through one of these career paths. If you want a full-stack marketer with proven experience in these domains, know that it may take longer to find and command higher compensation to recruit them. 
• Strategy vs. execution: Is it more important to bring on a seasoned executive who will be well-versed in helping to drive the direction of the business (along with necessary pivots) and a Rolodex of talent? Or are you willing to place your bet with someone who can critically think while rolling up their sleeves and can grow with the business? Founders should evaluate this tradeoff based on the marketing team's needs and the company’s position and runway. These two hires will require very different management styles from the founder and team support—choose honestly and wisely.
• Scalability over time: After evaluating your short and long-term needs against your runway, what are the critical gaps you need to fill? Are you willing to make tradeoffs between a seasoned executive who has primarily operated at established companies and a leader who has had at least one tour at a fast-growing startup? This element is usually the hardest to decipher because it also involves evaluating soft skills that determine how they get things done internally.

Combining these elements makes the role unique for your company while keeping everyone honest about what the company actually needs. It’s more often the case that startups are not ready for a CMO hire and should consider mid-level candidates for a Head of Marketing position that allows room for malleability on both sides.

My experience at EatWith is an ideal example. I left the rocketship that was Pinterest after serving as their first marketing hire for nearly four years because I was craving to build again at a Series A startup. I had a vision for a marketing strategy built alongside the CEO, but I wasn’t above pulling weekly reports and editing copy. My experience at big companies like Microsoft and Amazon allowed me to forge partnerships with key brands such as TripAdvisor and MasterChef, while my experience with scaling at Pinterest prepared me to pivot quickly when necessary. We ultimately positioned the company for acquisition.

Advice: Founders must define the role’s priorities before hiring. Start by evaluating your current challenges—whether they are awareness, driving acquisition, or product adoption—and assess them against the medium- to long-term needs of the business. Then, align these needs with the candidate’s expertise.

3. Under-resourcing the Role

A strong CMO can’t thrive without the right tools, team, and budget and appropriate time to define and implement them. Too often, startups hire a marketing leader but fail to provide the resources and patience needed for success. It’s like buying a luxury car or home at the base model without any of the “bells and whistles” upgrades. As a result, even the most talented CMOs end up constrained by organizational bottlenecks, getting in their own way of success.

Here are common traps:

• Tools: Will this role require the implementation of new tools, such as CRM and analytics, along with support from engineering? Finding and implementing platforms can take up to 3 months or more; is this timeframe something you can afford? Founders must be ready to drive cross-functional accountability to ensure that marketing, engineering, and product teams are aligned to the same goals. 
• Team: Do you want this role to hit the ground running and immediately drive measurable results? If so, you may reconsider what you’re hiring for in the new hire. CMO and most Head of Marketing roles will need to ramp up a team of in-house ICs, agencies, or freelancers. Before the recruiting process begins, you will also need to consider time for this role to audit the business and time to align with founders on the hiring plans.
• Budget: Have you looked at your forecast and considered various scenarios with and without this role (along with the cost of tools, hiring, and other marketing costs such as media)? The inputs and outputs of the role should pass your financial stress test, not just the cost of the hire itself.

Advice: Before hiring, ensure you can allocate sufficient resources to the marketing function. Resources may include funding campaigns, building a team, and enabling access to necessary tools and data. If you don’t have the proper runway or time to see a holistic marketing strategy to fruition, consider hiring strong ICs with the potential to rise to the occasion who can primarily focus on delivering immediate results. 

Part Two: What Candidates Get Wrong

1. Overestimating Influence

Candidates frequently assume they’ll have decision-making power over critical aspects of the business. However, in startups, marketing is often sidelined in favor of product-driven growth or priorities of the sales team. This dynamic can leave CMOs feeling disempowered and frustrated.

Here are important areas to dig into:

• Product roadmap: What is the role of product marketing, and when does marketing get involved in the product development process? What is the usual cadence or lead time before a feature goes to market? Marketing should be able to drive or participate in user research once the product team has decided on a feature. The role clarity will help ensure that customer feedback is incorporated into positioning and messaging, which is a critical step in the GTM process. 
• Current sales pipeline: Is the customer journey mapped? Is there a RevOps function that supports handoffs between marketing and sales? Who owns sales enablement? When a company is primarily B2B or has a B2B side to its business model, marketing will likely drive leads. Understanding the sales team's expectations and what levers are already in place will be helpful.
• External and internal comms: PR is an ever-changing function as more founders are leaning into their role as the face of the brand. It is also essential for a brand to have a unified front regarding messaging, with clear ownership of who is driving the narrative across multiple audiences. 

As a marketer, treat this exercise like you understand your audience—with other execs in an early-stage startup. You must ask the tough questions that help you understand how teams align their strategies towards the same north star. You also have to be aware and honest about the role that marketing should play. If it’s a product-led growth business model, marketing will be expected to maintain a lower CAC than the industry norm and remain hyper-focused on user experience regarding communication.

I’ve observed this disconnect many times throughout my career. Common pitfalls include marketing teams owning only the “outbound” side of product launches, preparing sales collateral before aligning on the target audience, or lack of collaboration between PR and marketing on any narrative. I’m not dogmatic about organizational structure or span of control, but collaboration is a must in these disciplines. 

Advice: During the interview process, candidates should assess how marketing fits into the company’s overall strategy. Questions like, “What percentage of revenue is allocated to marketing?” or “How does marketing collaborate with sales, product, and PR teams?” can reveal valuable insights. Make sure to meet with key stakeholders with these teams and get a complete picture—not meeting them or last-minute changes to the organizational structure can be red flags. 

2. Underestimating Startup Challenges

Transitioning from a large organization to a startup can be a shock. In resource-constrained environments, CMOs must balance strategic planning with hands-on execution. Candidates accustomed to delegating tasks may need help in these conditions.

Sometimes, the founder or organization may need to know the soft skills needed to strike this balance well. Lots of introspection is required—candidates also need to take ownership of their destiny. Here are some questions to consider:

• Do you have tough skin? Are you able to proactively seek and receive critical feedback, even if it’s in real-time?
• How do you deal with change? Can you thrive in ambiguity? Do you get energized by driving solutions, even when situations seem impossible?
• Have you talked to other startup marketers about their challenges and learnings? 
• Would you consider taking the job if there was more equity than cash? While I don’t advocate for this, I find this question to be a good barometer for gauging your intrinsic motivations for joining a startup.

Advice: Candidates should evaluate whether they’re ready for the scrappiness and adaptability that startups demand. Highlighting experience in both high-level strategy and tactical execution during the interview process can position you as a better fit.

3. Ignoring the Importance of Timing

Joining a startup as a CMO at the wrong growth stage can be career-limiting. If the company hasn’t achieved product-market fit or secured funding, the marketing function may lack the foundation for success. A common question you might hear is: "Should we invest more heavily in brand or growth marketing? If both, what's the balance?"

This is the classic chicken or egg question faced by founders and marketing leaders.

As with all great questions, the answer is "it depends." It can determine the impact of a marketing leader’s role and other variables that I share in this Reforge event. The table below summarizes the marketing type that a company might need at different growth stages. It’s not a perfect science, but it gives you a sense of the realities behind the CMO function.

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Advice: Candidates should carefully evaluate whether the startup’s stage aligns with their skills and expectations. Early-stage startups might benefit more from a generalist or fractional CMO, while growth-stage companies can better support a full-time leader.

Part Three: The Reality of the Role & How to Get It Right

The CMO role is a delicate balance of strategy and execution. While long-term planning is essential, startup CMOs must dive into day-to-day tasks, from writing copy to analyzing campaign data. As the first marketing hire at Pinterest, I experienced this duality firsthand—juggling immediate needs while laying the groundwork for scalable growth.Marketing doesn’t exist in a vacuum. Successful CMOs align their work with product, sales, customer success, and PR teams. However, cross-functional collaboration often poses challenges, particularly when goals are misaligned, or communication is lacking.

One person can’t solve everything, and it is incumbent upon both the founder and CMO to build a culture where alignment is critical and teams can adapt to the ever-changing needs of a fast-growing business. Here are some ways to get it right:

For Founders: Building a Framework for Success

1. Define the role clearly: Using a structured approach to define the scope of the CMO. Will they focus on demand generation, product marketing, or brand strategy? Clarity reduces misalignment and improves hiring outcomes. Also, organizational structures should be created that encourage collaboration, such as shared KPIs or cross-departmental meetings.
2. Evaluate readiness: Ensure your startup is ready for a marketing leader. It is often better to start with strong ICs who are marketing generalists or a fractional leader before hiring a full-time CMO.
3. Provide resources and autonomy: Set your CMO up for success by equipping them with the proper budget, tools, and decision-making power.
4. Balancing strategic vision with execution: Seek candidates who thrive in ambiguity and can switch between tactical and strategic thinking.
5. Have empathy and know your tradeoffs: The unicorn you’re searching for may not exist. Marketing spans several disciplines, and it will be impossible for a single person to be an expert in every area. Be honest with your must-haves vs. nice-to-haves, and be on the lookout for someone with a growth mindset.

For Candidates: Navigating the CMO Journey

1. Do your homework: Research the startup’s stage, culture, and challenges. Ask tough questions during interviews to ensure alignment.
2. Build for the long-term: Recognize that your success depends on developing scalable strategies. Focus on creating systems and frameworks that outlast your tenure.
3. Align expectations: Clarify priorities and metrics for success early on in the process. Misaligned expectations can derail even the most promising opportunities. Highlight your experience working across teams and your ability to unify stakeholders around a common goal.
4. Juggling strategy while driving impact: Showcase your ability to operate across multiple levels of responsibility and be prepared to scale yourself more than you would at a mature org. Look to systems and lightweight tools to help you in lieu of more headcount.
5. Embrace your role as a teacher: While everyone will have an opinion on marketing, it is the CMO’s job to educate people along the way. This includes the founder, board members, and other executives. Have patience and exercise your skills as an effective storyteller. 

The Future of the CMO Role

The CMO role is ever-evolving. From my vantage point, after a mix of successful startups and broken pickers, it all boils down to mutual fit and one’s ability to be introspective. It’s also worth acknowledging that there is no perfect science when it comes to hiring for this role, but hopefully, this post gives you a helpful framework to evaluate your tradeoffs and empower your decision making.

There is a changing landscape of the work environment to consider as well. Companies are expected to deliver more with fewer resources, while employees seek alignment with personal values and better work-life balance. The Great Resignation has evolved into a new cultural trend of reshuffling priorities and identities no longer tied to work, leading to a higher demand for hybrid solutions and portfolio-based careers. 

Overall, it seems so simple but incredibly hard to get right. Both founders and candidates need to recalibrate their expectations and approaches to succeed. By understanding the realities of the role, avoiding common pitfalls, and fostering strong partnerships, startups and CMOs can drive meaningful growth together.

As an optimist at heart, I am hopeful that there will be a new pattern in the tech scene—founders and CMOs as the necessary and furious duo behind challenger brands, the most incredible brand comebacks, and innovation-driven growth. 

About the Author

Annie Katrina Lee is a Fractional CMO, Advisor, and Co-Founder of Penknife Collective. As a thought partner to founders, she offers honest guidance and pragmatic creativity to address their marketing needs and organizational design. She draws from her experience as an early employee and first marketing hire at Pinterest, along with leading teams at Amazon, Twitch, and numerous startups. 

About RevelOne
RevelOne is a leading go-to-market advisory and recruiting firm. We help hundreds of VC/PE-backed companies each year leverage the right resources to achieve more profitable growth. We do 250+ retained searches a year in Marketing and Sales roles from C-level on down for some of the most recognized names in tech. In addition to our Search Practice, our Interim Expert Network includes 250+ vetted expert contractors – executive-level leaders and head-of/director-level functional experts – available for interim or fractional engagements. For help in any of these areas, contact us.