After having worked fractionally for three years, in the first half of 2026, Kate executed 25 targeted prospect outreaches, resulting in four clients. Knowing you're going for a, say, 15%-20% hit rate makes the 25 outreaches feel crucial, rather than fruitless.

Each week, Alaina ran 2 to 3 catch-up calls with old contacts. She estimates a roughly 5% conversion, but she enjoyed them and this made the volume sustainable. She was open and learning, and that energy came back.

Not every at-bat looks promising up front. Alaina was a Haldi skincare user, cold-messaged them through the customer service portal because she loved the product, and over the course of a few months, they became a client.

The at-bats that more typically convert fastest are warm, friend-to-friend intros, where the person arrives ready to decide rather than comparison-shopping. Cold inbound is the highest-volume, lowest-yield channel.

Relatedly, old colleagues are almost always the right first calls. They'll be willing to reach out to others or their own teams on your behalf, which can have the same effect as a back-channeled reference. A version of this may also be your current employer: when you leave, there's real work left on the table and backfilling takes time, so a part-time continuation is a soft landing for both sides. This was something I struggled with at Alchemy, but it's a great option if you can make it work.

Alaina's first client came wanting a full-time Head of Marketing. She counter-pitched a fractional CMO scope, then built the five tranches of work with the founder (marketing P&L, board prep and fundraising, strategy and content, growth and paid media, production), framing it as product-market fit between her and the company. For the founder it was "half the budget, all of the value."

Faith recognizes that companies often know they have a gap but can't name the skillset, so the operator who can define the actual work has the advantage. Starting conversations from a "discovery" standpoint can lead to you knocking their socks off in the first follow-up with a clear diagnosis of what they need (and ideally why you’re right for that scope). 

Kate sets the gold standard of charging what you're worth. As she reminds us, a full-time, executive level Head of People position may read as $200-$250k, or the equivalent of $100-$125 per hour. But what this omits are the meaningful equity grants, benefits, retirement contributions, perks and tax contributions she is earning, that have a meaningful associated dollar value, and aren’t paid to a 1099 worker. Accordingly, even a mid-level 1099 contractor typically makes ~10% more per hour than their in-house counterpart. 

Her deeper point is compressed experience: an in-house hire has perhaps run the playbook once or twice, in one or two contexts, but an experienced fractional has run it across dozens of companies. The pattern matching they can do is similar to a specialist surgeon who has done a hundred instances of a single surgery, versus a generalist who will be doing it for their first or second time. They know the exact shape of a specific set of problems and because of that, they can move meaningfully more quickly.

Relatedly, early-stage founders care about growing revenue, getting efficient, hitting the next milestone, and burning less cash. In these scenarios, sell the outcome, not the time, with a value-based compensation rate. This could be something like: "My monthly retainer to deliver our 6 month roadmap is [x] and this project will increase your runway by [y]."

Take the bet of charging upfront - they are investing in your capacity and value contribution. Too many fractional leaders invoice in arrears, NET30. That means you are paid up to 60 days after adding value, and reserving capacity for a client. In 2 years Kate has only had one client push back on invoicing each month due on receipt.

When leveraging outcome-based pricing, tactically, Alaina structures it as 50% of the project fee up front and 50% on completion, treated as a mutual test. From there, she prefers to transition to an ongoing, monthly retainer.

Alaina learned from a few mistakes to get here. When she started out, she priced her first two retainers too low, then needed to supplement her time with random, hourly work. Going into year three, she doubled her retainer and stopped asking "This is an ideal client, what will they pay me?" and started asking "I need to make [x], who will pay me that?" And went and found them.

Even though the outcome-based logic above is right, I'll admit the hourly structure has its charms. When I worked as part-time Head of Marketing for a Seed-stage fintech company, I enjoyed the combination of outcome-based goals and an hourly payment structure. It made it feel like when I was working at 4pm on a Sunday, I was literally making money and that was motivating.

Whether to take equity is (unsurprisingly) shaped by the stage and trajectory of the company, but there's a cleaner way to think about it, courtesy of Darin Swanson, via Kate: equity is long-term value, and most fractional or project work is short-term, helping a company cross a chasm from zero to one, or one to ten. When the engagement is short and the value you add is immediate, cash is what actually matches the work. From Alaina's perspective, after taking options at two very early-stage clients that didn't pan out, she no longer considers it. As she says, "I'm not a VC. I'm a paid employee."

There's a real exception. If you have conviction a company has legs, "there's a real there there" from Faith's perspective, equity can let you work at an interesting startup at a stronger effective rate than cash alone. Two cautions: taking equity into an LLC rather than as an individual can create real tax headaches when it materializes, so get advice first, and you can lose credibility fast if your ask is wrong for the stage, e.g., requesting a ludicrous number of basis points from a seed-stage company.

One useful middle path: for a company you believe in that genuinely can't pay cash yet, you can offer light advisory equity using a public template like the FAST agreement, then move them to a cash retainer as they gain traction. Something like a one-year advisory role capped at 20 hours, no more than two a month, for 10 basis points.

Alaina caps herself at two clients at a time. She found that if she peppered in a couple hours a week with two additional clients, it would inevitably feel like being split four ways, even if it was two mains and two littles. As she puts it, "my clients suffer even from an hourly relationship on the side." Saying no to the extra work is how she stays good at the work she already has.

Kate agrees. She limits herself to 1 major and 2 minor clients at any given time. With a fully-embedded model with early-stage clients, knowing context inside-out and being available for fire drills is critical. Embedding this way is not possible across more companies without compromising quality. Therefore each retainer has to be large enough to fit into this model. Kate passes smaller, project-based engagements to fellow fractionals, and aims to either hire an FTE for growth-stage companies who need ongoing senior support, or introduce one of her mid-level sub-contractors for 'run the business' support for those in steady-state.

This is a big one. A huge theme I heard when researching Groundwork was this desire for individual contributor work (i.e., non-management work). The reasoning makes sense: if I’m managing everyone at home, I don’t have the bandwidth to manage lots of personalities at work, too. So when going part-time, favoring these individual contributor roles is a smart north star. 

Relatedly, look hard at how much of the role depends on things you don't control. A Customer Success Team Lead role might be available part-time, but if your work is contingent on an unvetted team, you may not have enough control to do it well. It might work, but dig in first.

Be diligent about the recurring meetings you allow in. What context building is absolutely necessary for the best results? 

Faith's filter is a useful one here: map the work you love against the work you never want to do again, and scope your engagements around that. The more the role is built out of work you're good at and want to be doing, the better. Again, this is your business.

If you can, take at least one true operator role a year so you stay sharp on current tools and more in the weeds than an advisor.

Your job, in running this business, is to sell something of value to people who need it. And a piece of advice Kate shared is that early stage founders are over-advised and under-resourced. They need head and hands, not another piece of advice no one can execute against in the two weeks before the next advisor check-in. 

Being ready, willing, excited to roll up your sleeves is going to be crucial. 

The first year is for experimenting: try different pricing, models, client types, project versus embedded retainer work, and pay attention to what actually gives you energy. But run every engagement through one more filter, your values. Do you respect how this founder operates? Does the work energize you or drain you?

A misaligned engagement costs more than the income it brings in. Kate learned this the hard way. A quarter with a founder she was deeply misaligned with took a real toll on her wellbeing and her family, and because she kept over-delivering to try to win him over, it wasn't even good money for the hours. Worse, misaligned clients don't refer you to the right work, and the market reads who you work for as a signal of who you are.

So end misaligned engagements quickly, on respectful terms, and say no to misaligned income unless you're genuinely in a bind. This is the through-line of everything above: the point of building your own practice is that you get to choose, so choose for alignment, not just for the retainer.