How to get started as an interim CMO - Part III

The good, bad, and ugly of doing interim and fractional work

Happy New Year everyone! ✨🥂

This is my final post on the interim CMO series. My last two posts were about when founders should opt for an interim CMO and how to choose an interim CMO for your startup.

If you are a marketer exploring this path, temporarily or permanently, this post is for you. I cover how I got started, lessons learned, mistakes made, tips for getting started, risks of fractional work, and how to think about pricing.

Start from purpose 💓

I became an interim CMO in 2015 after eight years in marketing leadership and fifteen years of marketing in tech. In multiple startups, I noticed a recurring pattern:

• Even as they scaled, their marketing function remained at an early stage.

• They lacked a solid marketing strategy, including positioning, branding, and go-to-market plans.

• They often had the wrong people in the wrong roles.

• Their product, marketing, and sales teams were misaligned.

I found myself spending the first few months putting a lot of these foundational blocks in place before I could do the job I was hired for — growing and scaling the business.

I thought if I could work with early-stage startup founders to help lay down a strong marketing foundation, I would not only be doing my craft and profession justice, I’d be helping founders understand what good marketing looks like, and I’ll also be paying it forward to the future VPs and CMOs of that startup.

This was my primary motivation to go out on my own. Not freedom. Not flexibility, Not optionality.

Don’t get me wrong, I have all three, but those are simply byproducts, not the catalyst for what I do.

A tiny word of advice: If you choose to go down this path, take a long, hard look at your motivations. Is it shiny objects like independence, money, freedom, and flexibility, or something deeper, like a true purpose? Something you passionately believe in and care about? If you stay anchored in that belief, you’ll stick with it, no matter the ups or downs.

Find your fit 🫱🏾‍🫲🏽

You are no different than any other early-stage startup venture. You’re not taking capital, and maybe you don’t have employees on payroll, but other than that, everything else is the same!

It took me two years to find my fit. I created hypotheses and experimented with:

• Size and stage of startups

• Categories - B2B, B2C, and marketplaces

• Technical and non-technical products

• Growth vs. brand vs. operations

I sucked at some things, and I was very good at others. I honed in on what I did best and what gave me the most satisfaction. I created hypotheses, and every interim gig helped me prove or disprove a hypothesis.

Start small, under-promise and over-deliver 🎉

The first few startups I worked with, I was 100% dedicated to them. I did not juggle two or three startups as I can easily do now, only because I’ve built the muscle for it over the years and I have a set of methodologies, frameworks, and best practices I can apply across different startups.

Before I got here, I slogged it out one startup at a time. I learned a lot about where I add the most value, when I was better off delegating to other experts, and how to manage founders’ expectations.

Word of mouth matters 🗣️

I have only one main goal with my practice — 100% reference from founders and VCs of startups I’ve supported. My practice depends entirely on WOM and the relationships I’ve built in the tech community. Besides this newsletter and occasional LinkedIn posts, I don’t do any “marketing” of my services. The tech community is small. Founders and VCs know one another. If you do good work, your founders and VCs will think of you when they come across a startup that could use your expertise.

Feast, famine, and everything in between 🍛

When you start out as a solopreneur, you must be prepared for periods of abundance and scarcity. When it rains, it pours is true when you’re self-employed. When things are slow, and tech goes through a period of turmoil, like now, many people want to do interim work. Competition increases, and startups tighten their purse strings. That’s part of the cycle. Be prepared to weather the storms after days of endless sunshine, but also remember the sun will shine again. 🌞

Building any business takes time. I’m a big believer in the axiom, “Go slow to go fast.” Start small and slow. Make mistakes, learn, revise, repeat.

Plan ahead and always be in biz-dev mode 🗓️

This was something I failed to do early. When I started working with a startup, I was too focused on the work and did not think ahead of my pipeline. This created unwanted gaps in my pipeline. Now, I plan a quarter ahead and book my engagements a month or two ahead of time.

I must remind myself to keep putting myself out there, talking to founders and VCs, attending events, and networking. Being an introvert, this is not my favorite part of the job, and I’m still working on getting better at this.

Think about scale early 🧗🏽‍♂️

Every startup you’ll work with is unique. I’m not a playbook marketer. I don’t believe in it. Not everything that works for startup A works for startup B. However, there are sound principles that apply across the board. After every interim project, I do a retrospective. Often, I think of a different way of framing an idea or a principle. Over time, I codify these as frameworks, methodologies, templates, and cheat sheets. This helps me onboard myself quickly, add value fast, and deliver outcomes without reinventing the wheel every time.

A few tips for getting started 🏃🏽‍♀️

• Start with your current network. They know you and can vouch for your work.

• Talk to advisors and venture partners who might come across opportunities and connect you.

• If you see startups looking for a full-time head of marketing and you know someone who works there, reach out for an informational chat. You might learn something about their particular challenges, and perhaps you might have something to offer.

• Attend local tech meetups, happy hours, and conferences.

• Offer to do a lunch and learn or a workshop at a friendly startup on a subject matter that would be valuable to them.

• Take every introduction! I mean this. Even if all they do is get your advice for thirty minutes, it’s still worth it. First, you leave a good brand impression. Second, you never know when they might need help or who they might know.

• Finally, be generous with your knowledge and time. Remember, you’re just getting going. The more people you meet, the more connections you make, the more value you add, and the more likely they are to refer or work with you.

The risks of fractional work 🌓

I mostly do interim work or project-based work. I avoid fractional work for the following reasons:

• Boundaries — It’s hard to do fractional work for early-stage startups. If you work only two days a week for a startup, and something goes wrong on a day when you are not working, who’s going to respond to that crisis? Most likely, it’ll have to be you. I found it hard to draw boundaries with early-stage startups. Fractional works better at a later stage (series B+). If you have a different experience, please comment below! I’d love to learn from you.

• Accountability — When I work just half-time for a startup, it’s hard to be accountable for the entire function. Unless there’s a strong team executing and your role is one of guiding/supporting, it’s hard to deliver results half-timing it. Ultimately, those results are why they are bringing you on board. It’s a catch-22, IMO.

The good, bad, and ugly of interim work 👍🏽👎🏽

The good — To me, there’s nothing more satisfying than taking on a startup grappling with a challenge, and working together to help them resolve it. Coming out the other end with a successful outcome that the founders feel excited about is truly the best part of my job. I also love being in charge of my future and working with a variety of startups in different categories. I’m always learning, which is a terrific feeling!

The bad — There is no steady paycheck here. No certainty on how the interim work will go. There is no guarantee that the startup will succeed, even if my work is good. I have to always think about my pipeline and do the legwork for it.

The ugly — In the early days, I misjudged scope and fit. I did not pay attention to founder chemistry and whether we saw eye-to-eye on how marketing should be done. This came to bite me later. I’ve become better at this. I’ve learned to interview founders as much as they interview me. This is the “art” part of this job. You have to not only be a marketing expert but also a guide, coach, and advisor to the founder on all kinds of strategic decisions that may impact growth. Building trust is crucial, and judging fit early is critical. Having a few uncontested wins early helps a lot in establishing credibility.

A word on pricing 💰

I typically price interim work as a monthly retainer plus equity. I’ve noticed a pattern. In good times, founders want to pay in cash and not give me equity; in bad times, they want to pay more equity and less cash. It makes sense, and you must work out the right balance for you and them. Typically, the options should vest monthly and not have a cliff.

Some people sign on as a W2 employee. I don’t do this. It becomes hard to part ways when you’re 100% engaged as an employee, especially at an early-stage startup. I’m sure it has its advantages (healthcare and other benefits), but the role is “interim,” part of the job is to have an impact quickly, help hire a full-time CMO, and transition smoothly.