Forty Consultants Later

What one business that's hired dozens of independent consultants actually looks for

Most of the conversations I have on this Substack are with consultants. We talk about how to find clients, how to price work, and how to build a pipeline, but we’re always sitting on one side of the table.

I wanted to hear from the other side. Sasha Rosen and I have been friends since 2006. We have two decades of working in overlapping corners of the political and organizing worlds, trading notes, pushing each other, and watching each other build things. Sasha is the CEO of The Outreach Team, which she has grown it into a national force in civic engagement, running grassroots campaigns on clean energy, reproductive freedom, democracy reform, and more across 25-plus states. Before that she built and led two other field companies from the ground up, and along the way has employed well over a thousand people.

Sasha is one of those leaders whose ambition is quiet and whose judgment is loud. She is the kind of person who hires a consultant to help her figure out whether she needs a full-time CFO, and then trusts the answer when it's no. Over the past six years, her team has brought on somewhere between 40 and 50 independent consultants. In 2024 alone, they hired about 15 business development consultants, plus a fractional CFO, DEIJ consultants, and others. I don't know anyone on the client side with more firsthand experience hiring, managing, evaluating, and yes, firing independent consultants.

So I asked her: how do you decide you need one? What do you look for? And what makes the difference between someone who earns more work and someone who quietly gets let go?

When a Full-Time Hire Isn’t the Answer

Sasha’s team first turned to consultants in a serious way in 2023, when they identified business development as a strategic weakness. They were strong at running campaigns but lacked access and influence in enough places. The initial instinct was to hire someone in-house. That didn’t work, because the problem itself didn’t have a single-employee shape.

“We realized it’s not that we just need one person,” Sasha told me. “We need multiple people with different expertise in different states with different networks.”

The same logic applied when the team identified a gap in their financial systems. They considered hiring a full-time CFO or controller and even talked to a headhunter. But the headhunter asked what they were looking for, and the answer was: we’re trying to figure that out. So they hired a consultant to define the need itself, build the systems, and serve as a stopgap while they determined whether a full-time role even made sense. In the end, it didn’t, and that same consultant remains as fractional CFO.

The pattern Sasha described comes down to three categories. First: project-based work with a defined timeline, where you need outside expertise to solve a specific problem. Second: strategic or structural questions where an external perspective — someone who knows how other organizations operate — is the whole point. Third: highly specialized access, where the consultant provides on-the-ground intelligence and relationships in a specific geography or field. In that third category, Sasha hired someone in Maine who provides access to key decision-makers and real-time intelligence on what’s happening across C3 and C4 tables — the kind of knowledge that would otherwise require a full-time state director, but then that person wouldn’t have enough else to do.

What struck me is how specialized these needs have become. A generalist business development hire was never going to work, given how narrow and varied The Outreach Team’s work is across different states. Consultants allow for diversification of expertise in a way that a single full-time role never could.

The Networking Tax

I asked Sasha how she actually finds these consultants. The answer was immediate and unsurprising, but still worth hearing from the client side: it’s all relationships.

Almost every consultant her team has ever hired came either from someone they already knew or through an introduction from a trusted contact. They’ve issued an RFP exactly twice, and even those went out through networking. “There are no good listservs for consultants,” Sasha said. “I always feel bad about that, because if I were trying to sell myself, I don’t know where I’d go. It’s just networking. That’s all it is.”

This tracks with the research we published last summer, where consultants reported sourcing essentially all of their engagements through their personal networks. But hearing it from the buyer confirms something important: the networking isn’t optional, and there is no alternative channel waiting to be discovered.

Sasha did add a nuance, though. Most of the time, her team isn’t even actively looking for a consultant. Someone pitches an idea during a conversation, and the team decides to bring them on for a discrete project. The business development consultants were the one exception — a genuinely intentional search, where they even hired a separate consultant to identify the right people in specific states.

So the hiring process, most of the time, is less like a job search and more like a relationship that crosses a threshold.

What Gets You Hired (and What Gets You Kept)

When Sasha evaluates a consultant, she’s not usually comparing three candidates against each other. She’s evaluating one person against the job. The two things she looks for: previous experience doing the kind of work needed, and trusted people who vouch for the person. That second one is less about formal references and more about knowing someone real in the world who says this consultant is legitimate and won’t waste your money.

Sasha was candid about the hit rate. Of the eight business development consultants hired in 2024, about five — roughly 60% — actually delivered business. The rest didn’t produce. One consultant demanded a high upfront retainer and high referral fees. In retrospect, Sasha sees that as a red flag. For business development work, the ideal structure is a low retainer and high referral fees, tying compensation directly to the consultant’s ability to produce. Asking for both signals that the consultant wants to get paid regardless of whether they deliver.

What determines whether the relationship continues is simple and unsentimental: short initial contracts, clear deliverables, and observable results. Consultants who deliver often get extended to ongoing contracts. Those who don’t are let go. “If you just do your job, there’s usually more money and work to be had,” Sasha said. “The problem is when you don’t do anything.”

Pricing Negotiations

The most revealing part of our conversation was about pricing, and it centered on a consultant who has become something of a model engagement.

Sasha first hired this consultant on a three-month contract for $12,000 total, which she considered an excellent deal. Based on this person’s performance, the next contract was six months at $5,000 a month. When the third negotiation came around in December, Sasha had mentally budgeted $8,000 to $10,000 a month and was ready to nearly double the consultant’s rate. Then they proposed $12,000 a month.

Sasha negotiated down to $10,000. She now regrets it. “This person is worth way more than $12K a month,” Sasha told me. She plans to give the consultant an additional bonus at some point as a retroactive thank-you.

The lesson for consultants: ask for what you’re worth. Sasha’s words, not mine. “If you don’t ask for it, you won’t get it. People will just say no if they can’t do it.”

Sasha expects consultants to cost more than an equivalent in-house person — that’s built into her mental model. She’s covering less of the consultant’s time, so the hourly or monthly rate should be higher. What she doesn’t want is to feel gouged.

Sasha’s strong preference is for retainers or lump sums over hourly billing. She doesn’t want to monitor how much time someone spends on a task. She wants the job done, within the agreed-upon timeframe, for the agreed-upon price.

The Mistakes That End Contracts

I asked Sasha about the most common mistakes consultants make. Three came up repeatedly.

The first is failing to communicate about availability. Consultants have other clients. Sasha knows this and accepts it. But she needs to know when someone will and won’t be responsive, especially for time-sensitive work. The consultants she values most are the ones who proactively flag their schedule and set expectations. The ones who annoy her most go quiet without explanation.

The second is more basic than you’d think: some consultants get hired and then never reach out. No meeting set up. No check-in. Sasha has had consultants who were on a retainer and simply didn’t initiate contact for two months. By the time they circled back asking what she needed, the answer was: nothing anymore.

The third ties pricing to attention. One consultant on a $1,000-a-month retainer never did much of anything. Sasha suspects the fee was too low for the consultant to prioritize the relationship. The lesson cuts both ways: if a retainer is so small that you’re not going to pay attention, don’t take the money. The retainer exists so you pay attention. If it doesn’t accomplish that, the whole arrangement is pointless.

The Advice

I asked Sasha what she’d tell any consultant who wanted to work with a firm like The Outreach Team. She was direct: don’t send cold pitches, understand the organization’s actual business and whether your services are relevant, and connect through an existing relationship.

And then the part that most consultants need to hear: don’t get discouraged by slow responses. Sasha acknowledged that her team often recognizes the value of what a consultant is offering but doesn’t have the bandwidth to act on it. The issue is timing and capacity, not disinterest. Consultants who stay in touch and nurture the relationship — without being pushy — are the ones who are top of mind when the timing finally aligns.

“Nine out of ten of the most important factors are just timing,” I said to her. Sasha agreed. “So that when the timing is right, they think of you.” That’s the whole game.

Which brings us back to the truth that runs through every conversation we have in this community—there is no substitute for relationships, and the work of maintaining them never stops. Sasha, who hires consultants all the time, described her own business development process in almost identical terms: go meet people, get on their radar, and reach out when you hear something relevant. It’s just as hard for the buyer as it is for the seller. The only difference is who’s sitting on which side of the table, and even that changes more often than you’d think.