Frequently Asked Questions
Everything you need to know about working with Stafford Strategies.
Services
A full-time VP of Sales costs $150K to $250K a year in salary alone, before benefits, equity, and ramp time. And if you hire the wrong one, you've lost six months and a significant amount of money finding out. Fractional sales leadership gives you the same level of experience and ownership, at a fraction of the cost, without the long-term commitment. I work with a small number of clients at a time, which means you get real attention, not a consultant who shows up once a month with a slide deck. The difference isn't just price. It's that I'm actually in it with you.
It depends on the engagement, but typically it means I'm in your CRM, on your team calls, reviewing pipeline with your reps, and holding the same accountability conversations a full-time sales leader would. I'm not observing from the outside and sending recommendations. I'm running the weekly sales cadence, coaching individual reps, sitting in on deals when it matters, and building the process your team will own long after I'm gone. I work the way an operator works, not the way a consultant works.
If you're pre-revenue and still figuring out whether you have a real product, I'm probably not the right call yet. Same goes for companies looking for someone to just hand them leads or close deals for them. That's not what I do. I'm also not the right fit if you're not willing to change how things are currently working. The companies that get the most out of this are ones that know something is off in their sales motion and are ready to fix it. If you want someone to validate what you're already doing, that's a different kind of engagement than what I offer.
Pricing
Engagements start at $2,500 a month for strategic advisory work and go up to $8,500 a month for a fully embedded fractional VP of Sales role. The right tier depends on where you are, what you need, and how much of my time makes sense for your business. If you're not sure where to start, the 90-Day Revenue Jumpstart pilot at $4,500 a month is designed exactly for that situation. Every engagement starts with a conversation to figure out what actually fits before either of us commits to anything.
Because an hour here and there doesn't fix a sales problem. It just creates the feeling of momentum without the actual results. Real change in a sales org requires consistency, context, and follow-through. You can't build a repeatable process in one-off sessions. Hourly work is available to existing retainer clients for overflow needs, but it's never how I start a new relationship. If someone isn't ready to commit to a structured engagement, we're probably not the right fit for each other yet.
It's a structured three-month pilot for companies that want to see what working together looks like before committing to a longer retainer. Month one is diagnosis: we figure out exactly where the sales motion is breaking down. Month two is execution: we build and implement the fix. Month three is optimization: we refine what's working and make a clear recommendation for what comes next. It always ends with a retainer recommendation, not a cliffhanger. It's designed for founders and CEOs who know something is off but aren't ready to sign a long-term contract before seeing results firsthand.
The tiers are fixed because they're built around specific time commitments and deliverables. What's flexible is figuring out which tier is actually right for your situation. I'm not going to put you in an $8,500 engagement if $5,000 does the job. The goal is a fit that works for both sides, not a number that looks good on a proposal.
Process
The first two weeks are about getting oriented. I'm reviewing your CRM, sitting in on calls, talking to your reps if you have them, and mapping out where the sales motion is actually breaking down versus where you think it is. Those two things are often different. I'm not coming in with a predetermined framework I'm going to force onto your business. I'm learning your specific situation first, then building the approach around it. By the end of week two you'll have a clear picture of what we're working on and in what order.
It depends on where you're starting from, but the markers I care about are pipeline consistency, forecast accuracy, rep accountability, and whether the founder is still in every deal six months in. If you came to me because sales felt chaotic and dependent on you personally, success looks like a team that runs a real process without you holding their hand through every opportunity. Revenue growth matters, but it's a lagging indicator. The leading indicators tell you whether the engine is actually working.
Access and honesty. I need to see what's actually happening in your CRM, not a cleaned-up version of it. I need your reps to know I have real authority, not that I'm a consultant they can wait out. And I need you to be willing to hear things that might be uncomfortable. Sometimes the bottleneck is the founder. Sometimes the sales process has never existed and everyone has been pretending it has. The clients who get the most out of this are the ones who stay involved enough to stay aligned but trust me enough to let me lead the work.
Most clients who complete the 90-day pilot move into a retainer. Once the system starts working it becomes less about fixing problems and more about maintaining the standard, developing the team, and evolving the go-to-market as the business grows. The goal was never to be here forever. It's to build something that doesn't depend on me. But in practice, having an experienced sales partner in your corner tends to be something founders want to keep once they've seen what it changes.
Working Together
I keep the roster small on purpose. The whole model breaks down if I'm spread across ten clients and nobody gets real attention. I work with a limited number of companies at any given time, which means when you're a client, you actually have access to me. Not an account manager. Not a junior consultant. Me. That's the point.
My deepest experience is in SaaS, cybersecurity, medical, and technology, but I don't lead with industry. I lead with business model and sales complexity. If you're selling a considered B2B solution with a real sales cycle, multiple stakeholders, and a team that needs structure and leadership, the work translates regardless of the vertical. The fundamentals of building a repeatable sales motion don't change much from one industry to the next. What changes is the language and the buyer, and I pick that up fast.
Both. Some of my best engagements have been with founders who are still the entire sales team and need help building the process and hiring the right first rep. Others have come in with three to five reps and a manager who needs development. The work looks different but the starting point is the same: figure out what's actually broken before we start building anything.
I'd rather have that conversation early than let something drag that isn't serving either of us. If the engagement isn't producing what it should, we talk about it directly. That might mean adjusting the scope, changing the approach, or deciding together that it's not the right fit. I don't hide behind contracts and I don't let problems fester. If something isn't working, you'll hear it from me before you have to bring it up yourself.
General
No, and I'd be skeptical of anyone in this space who does. Sales outcomes depend on too many variables: your product, your market, your team, your timing. What I can guarantee is that I'll show up with the same intensity and honesty I'd bring if it were my own business on the line. I'll tell you what's working, what isn't, and what needs to change. I won't tell you what you want to hear to protect the engagement. If I don't think I can help you, I'll say that in the first conversation before either of us commits to anything.
Sales doesn't exist in a vacuum so yes, I get involved in both. I can help with go-to-market strategy, messaging, positioning, and lead generation through outsourced BDR management. I also work closely with marketing to make sure what is being generated at the top of the funnel is actually what the sales team can close. I'm not a marketing agency and I don't pretend to be, but if the handoff between marketing and sales is broken, that's squarely in my lane.
Most consulting firms send you a framework and a deliverables document and call it a day. I'm not built that way. I came up through sales, not through consulting. I've carried a bag, built teams from scratch, missed quota, hit quota, and figured out why both happened. That experience is what I bring into your business. I'm also not trying to build a massive firm with twenty consultants under me. I work directly with a small number of clients because that's the only way to do this right. You get me, not a methodology with my name on it.
Fill out the consultation form on the site and we'll set up a call. The first conversation is straightforward: I learn about your business, you learn about how I work, and we figure out together whether it makes sense to go further. No pressure, no pitch deck, no commitment required. If it's a fit, we'll both know it pretty quickly.