FAQs

A fractional leader is not an advisor, coach, or mentor. Read this blog post to learn what a fractional leader is and how the position compares to other roles.

A fractional Chief Operating Officer, or COO, is a thought partner and extra set of hands for a startup founder or CEO. The COO helps them grow and operate their business.

A fractional COO doesn’t just advise, share experiences, or ask good questions. They roll up their sleeves and do the work that results from their business insight. They work as part of the team, developing knowledge that flows back to the organization.

I help by immediately jumping in where needed. I collaborate with founders and CEOs on customer and product, provide fundraising support, and take on part or all of the business operations and go-to-market operations.

You may need help from someone like me when you need to get more done, you need to spend more of your time on the highest-value work that only you can do (growth, fundraising, engineering), you or the team are wasting precious time on solved problems or reinventing the wheel, the organization is moving too slowly, or the team is operating ineffectively.

One specific use case would be covering a founder or CEO parental (maternity, paternity) leave, or similar gaps.

A shorthand way to think about how I help is that:

• I add capacity to the organization. The team knows how to do everything it’s doing. It just needs more hands to get more done. So I add this scale.

• I add capability to the organization. The team is incredible, but there are experience gaps. So I add this scope.

There are lots of reasons. One of them is that many aspects of the hiring process and work today are broken. The fractional model addresses some of these shortcomings.

For example: the best way I’ve found to evaluate if someone is a fit for a role is by working together. Bringing on fractional support makes starting and trying out a new relationship easy (compared to interviews, sample work assignments, and reference checks).

I operate in the BtoC and BtoB spaces across industries (with particular experience in sports and health). I work with no more than three companies at any one time for at least six months each, for the equivalent of one or more days per week per company.

Companies typically have more than 10 and fewer than 50 team members.

I work with post-Seed to Series A startups and bootstrapped companies with similar growth ambitions. I’ve worked extensively with business SaaS and tech companies, but I don't work exclusively in those domains.

I work on-site, remotely, and hybrid. A long-time resident of New York City and Boston, I now live in Toronto and Michigan.

I'm a hands-on, seasoned fractional COO (Feldspar, FreshAhead, Synervoz), sales coach (Microsoft), and mentor (High Alpha, Techstars). For over 20 years, I have applied my growth and operations skills to help dozens of startups (IAN, Axiom, Spartan). I began my career as a tech lawyer in New York City. I developed my expertise in progressive roles in business development, finance, sales, marketing and product, working along the way with companies like Amazon and IBM. So far, I have helped build one high-impact startup to nearly $100M in revenue and a second to exceed that benchmark.

In terms of formal educational institutions:

• New York University School of Law, JD, 1986

• Cambridge University (Peterhouse College), M.Phil., International Relations, 1993

• Cornell University, B.A., History, 1990

I have worked for and with established companies and startups, including 1 Hotel (Starwood Capital Group), Amazon, Axiom, Bose, Feldspar, FreshAhead, IBM, Internet Appliance Network, META, Microsoft, Spartan, Staples, Synervoz and Virgin. I have also worked on new ventures backed by investors such as 500 Startups, Benchmark Capital, EMC (now Dell EMC), Hearst Ventures and Union Square Ventures’ Fred Wilson.

I take a structured but flexible approach and don’t try to fit every organization into the same box. I am also guided by a flexible business framework—the Venture Plan on a Page—designed specifically and uniquely for post-Seed to Series A startups and bootstrapped businesses with similar ambitions.

Founders build sustainably successful companies when they keep the problem they solve for top of mind. This is the fundamental belief behind what I do. Accordingly, I take a structured end-to-end approach to:

• Understand the struggling moments that motivate customers to find solutions to problems.

• Build and improve differentiated products with distinctive sales and marketing that get the job done.

• Develop teams and align operations to deliver the desired product experience “every time.”

For my companies on a venture track, typically, the founder or CEO leads fundraising efforts. I will play a supporting role, helping to develop a strategy, research potential investors, organize and execute investor outreach, prepare and finalize presentation materials, and provide follow-up information. I’m also comfortable working with legal and other advisors on deal mechanics. This is basically a sales process, in which I have considerable experience.

I operate with a growth mindset and take a coaching approach to working with others, setting high standards and supporting teammates in reaching or exceeding those goals.

A few things.

First, I blend the best practices from startup land and corporate innovation programs. This comes from working on startup ideas at a big company, IBM, and startups at every lifecycle stage.

Second, I’ve worked on startups at every lifecycle stage, from a blank piece of paper to one startup earning over $250M in revenue. So I’ve seen where startups come from and where they are going.

Third, I have deep and extensive customer discovery skills. I am an expert interviewer capable of orchestrating an end-to-end customer insights project. When that is not needed, I still bring this customer-focused sensibility to all of my day-to-day work. I teach customer discovery skills to leading global companies through Somersault Innovation and write about these techniques and tools on Medium.

Fourth, in addition to my operations experience building on my early legal roles, I have an experience spike in sales. Consequently, this is an area where I can make an outsized contribution to growth initiatives.

There are four big reasons companies fail:

• They build the wrong product

• They pick a market whose size doesn’t meet their growth ambitions

• They run out of resources before they find traction

• They neglect company climate and culture, resulting in the organization unraveling at some future time

By knowing these pitfalls up front, we can take actions to avoid them.

I only do critical work that needs doing. I don’t look for problems to take on that don’t exist (to appear useful or fill time). We’ll start by co-developing a punch list of critical tasks, prioritizing a handful of high-impact “quick wins,” and then continuously and iteratively identify and address opportunities and problems to address to move the business forward.

You’ll finally get on top of the most actionable, highest-impact tasks I can take on to move the business forward.

I measure my success by speed.

Building high-growth businesses is hard. I can’t promise an economic success (a “big exit”). If I could, if anyone could, they’d be wealthier than anyone else in the world today.

I understand startups, though, and I understand what makes them succeed and what makes them fail. There are many unknowns and uncertainties at Seed-stage to Series A startups (and bootstrapped businesses that want to grow quickly).

So I measure my success as a fractional COO by how quickly I can help the organization move ahead during this fragile stage of life.

For example:

• For Build-stage companies that have not found product-market fit, this means more quickly finding product-market fit and a scalable go-to-market channel (or discovering we’re building the wrong product and pivoting).

• For Build-stage companies that have recently found product-market fit, this means more quickly harmonizing go-to-market and business operations to grow.

• For Scale-stage companies, this means more quickly hardening operations and hiring the executive leadership talent and other teammates needed to take the company through its next growth stage.

Because my time is normally fully utilized, I charge an amount that approximates the cost of a regular full-time employee (i.e., I don’t need to charge—and don’t charge—a big premium). I bill this amount as a simple daily rate plus advisor-level equity we agree on. The companies I work with generally do business in the US or globally, and I operate in US dollars.

Unlike some fractional executives, I’m not actively seeking a full-time role; however, if after working extensively together, we both came to the conclusion we were a perfect long-term match, I’d be open to joining a team full-time.

I’ve had the privilege of working for companies that have disrupted their industries and significantly and positively impacted their customers and the world. I’m always seeking out founding teams and organizations with similar ambitions.

An unexpected benefit of working with a fractional COO is just how incredible it feels (as a CEO or founder) to have someone working with you side-by-side in and on the business every day who shares your vision and commitment.