Fractional VP of Sales
Based in Charlotte, Working Across the US

Charlotte, NC (Home Base)

GSD Associates is based in Charlotte. This is home base, and if your team is here too, you get more of me in the room.

Charlotte-area teams get everything my remote clients get: weekly pipeline reviews, rep coaching on live deals, outbound strategy, hiring and a playbook your team can run. On top of that, you get in-person working sessions with you and your leadership team, an on-site kickoff to start the engagement, and ride-alongs on key deals, where I sit in on the meetings that matter and help your reps close.

Sales is still a contact sport. Being local just makes it easier to show up when showing up makes the difference.

In the Field When It Counts

I will help close deals, travel for in-person meetings, and attend trade shows with your team. A fractional VP of Sales should be in the game, not just calling plays from a laptop.

Travel is planned with you when we scope the engagement.

How Remote Sales Leadership Works

Most of the work happens week to week over video: pipeline reviews, call coaching, outbound strategy, hiring and the playbook itself. For kickoffs, sales team workshops, big customer meetings, late-stage deals and trade shows, I travel so we're in the same room.

The playbook is the same wherever you are. What changes from city to city is the buyer, the hiring market and the sales motion you need. Here's what I see in the markets I work with most.

Charlotte · Atlanta · Austin · Boston · Chicago · Dallas · Denver · Los Angeles · Miami · New York · San Francisco · Seattle

Atlanta, GA

Atlanta has quietly become one of the strongest B2B software markets in the country. Fintech, payments, logistics tech and supply chain software all run deep here, and the city keeps producing SaaS companies that sell to serious, operations-heavy buyers.

That's the challenge. Atlanta buyers are practical. They run fleets, warehouses, payment operations and field teams, and they don't buy on hype. They buy when a rep understands their operation and can show a clear return. Founder-led sales works early because the founder knows the product cold. It breaks when you hire reps who don't.

I've spent my career selling to exactly these kinds of operators, including in fleet and logistics SaaS. A fractional VP of Sales helps Atlanta founders turn what they know into a repeatable process that reps can run.

I'm based in Charlotte, a short flight or drive away, and I work with Atlanta companies remotely week to week. Pipeline reviews, rep coaching and deal strategy happen over video. For kickoffs, sales team workshops or big customer meetings, I'll be there in person.

Austin, TX

Austin has one of the most crowded startup scenes in the country. That's great for building a company and brutal for hiring sales talent. Experienced sales leaders get recruited constantly, and early-stage startups end up competing with well-funded later-stage companies for the same people.

The result: a lot of Austin founders stay in founder-led sales longer than they should, or hire a VP of Sales too early and pay for someone still figuring out the market.

There's a middle path. A fractional VP of Sales builds the system first (ICP, pipeline stages, outbound, discovery process, comp plan), so your first full-time hire walks into a machine instead of a blank page.

I work with Austin companies remotely, embedded in your Slack, CRM and pipeline reviews like a member of the team. Most Austin teams are hybrid or remote anyway, so this fits how you already work. When a kickoff or team workshop needs to happen in a room, I travel.

Boston, MA

Boston produces some of the most technical B2B software in the country, much of it born out of the area's universities, healthcare and research ecosystem. Founders here are often engineers or domain experts first, and they build products that solve hard problems.

The sales challenge is translation. Technical buyers want depth, economic buyers want ROI, and enterprise sales cycles run long. Many Boston startups have strong pilots and happy early users but struggle to turn them into repeatable revenue.

A fractional VP of Sales builds the bridge: a discovery process that finds the business case, a way to move pilots to paid contracts, and a pipeline you can actually forecast.

I work with Boston companies remotely week to week, joining pipeline reviews, coaching reps on live deals and building the playbook alongside your team. For kickoffs, board-prep sessions or major enterprise meetings, I'm happy to be there in person.

Chicago, IL

Chicago's software scene sells to the backbone of the economy: logistics, manufacturing, insurance, food and distribution. Many Chicago SaaS companies were built by founders who came from those industries and know the problem firsthand.

The challenge is that these buyers are skeptical of software sales pitches. They've been burned by tools that promised a lot and delivered little. They want a rep who understands their operation, can talk numbers and won't waste their time.

That takes a disciplined sales process: tight ICP, real discovery, and proof points that speak the buyer's language. A fractional VP of Sales builds that process and trains your reps to run it.

Most of the work is remote: weekly pipeline reviews, call coaching, outbound strategy and hiring. For kickoffs, trade shows and key customer meetings, I travel. Chicago's industry events are often where your best deals start.

Dallas, TX

Dallas–Fort Worth is one of the biggest corporate markets in the country. It's home to a huge concentration of large company headquarters, which makes it a strong place to sell B2B software and a tough place to sell it well.

Enterprise buyers here expect polished sales teams, clear ROI and strong relationships. Startups selling up-market often find their founder-led playbook doesn't survive contact with procurement, legal and a six-person buying committee.

A fractional VP of Sales helps DFW founders build the enterprise muscle: stakeholder mapping, business cases, mutual action plans and a forecast your board can trust.

I work with DFW companies remotely week to week and come on-site for kickoffs, team training and the enterprise meetings where being in the room makes a difference.

Denver, CO

The Denver–Boulder corridor has built one of the most founder-friendly startup communities in the country, with a deep bench of B2B SaaS companies selling to mid-market and SMB customers.

That community is a strength, but it also means many teams learn sales from each other rather than from operators who've scaled a sales org. The common result is lots of activity, inconsistent process and a forecast nobody believes.

A fractional VP of Sales brings the structure: defined stages, real qualification, a weekly operating rhythm and a comp plan that rewards the right behavior.

I work with Denver and Boulder teams remotely, embedded in your weekly rhythm. Remote work is already the norm for most Colorado startups, so this fits right in. For kickoffs and team workshops, I come to you.

Los Angeles, CA

Los Angeles has a large and growing B2B software scene, alongside the media, entertainment, e-commerce and consumer brands the city is known for. Many LA SaaS companies sell into those industries: creator tools, marketing and ad tech, commerce platforms and vertical software.

Those buyers move fast and expect a sharp pitch. They also churn fast when the product doesn't deliver. The sales challenge in LA is building a process that closes quickly without overselling, and hands customers to success teams set up to keep them.

A fractional VP of Sales builds that end-to-end motion: tight qualification, clear expectations in the sales cycle, and a clean handoff that protects retention.

LA is spread out, and most teams already run hybrid. I work with LA companies remotely week to week and come in for kickoffs, team workshops and the meetings that deserve a handshake.

Miami, FL

Miami's startup scene has grown quickly in recent years, with founders and investors relocating from other tech hubs. Fintech, proptech, logistics and companies selling into Latin America are all well represented.

Fast growth brings a specific problem: many Miami startups are young, and their sales functions are younger still. The local pool of experienced SaaS sales leaders hasn't caught up with the number of companies that need one, so founders often sell alone longer than they should.

A fractional VP of Sales closes that gap. You get an experienced operator building your sales process now, and a clear plan for the full-time hires you'll make later.

I work with Miami companies remotely, embedded in your weekly rhythm, and travel for kickoffs and key moments. If your market includes Latin America or other regions, remote-first sales leadership fits naturally.

New York, NY

New York is one of the largest B2B software markets in the world, with deep concentrations of fintech, ad tech, media, real estate and enterprise software. It's also one of the most expensive places to hire, and senior sales leaders cost accordingly.

NYC buyers are sophisticated and short on time. They expect reps who get to the point, know their industry and can prove value quickly. The bar is high, and a sloppy sales process shows immediately.

For companies between $1M and $10M ARR, a full-time New York VP of Sales is a big bet. A fractional VP of Sales lets you build the process, pipeline and team first, then make that hire with confidence, or wait until the numbers justify it.

I work with New York teams remotely week to week, with in-person time for kickoffs, team training and important customer meetings. You get senior sales leadership without paying a Manhattan salary.

San Francisco, CA

The Bay Area is still the center of gravity for venture-backed SaaS. Founders here often raise fast and face pressure to hire fast, including a VP of Sales well before the sales motion is proven.

That's one of the most expensive mistakes I see. A full-time VP hired too early spends their first two quarters figuring out the market, then gets blamed when growth stalls. The board loses patience, the VP leaves, and the company restarts.

A fractional VP of Sales de-risks that sequence. I help you turn founder-led wins into a documented process, hire and ramp your first reps, and define exactly what your future VP needs to walk into.

I work with Bay Area companies remotely, which fits the distributed teams most SF startups already run. I plug into your pipeline reviews, board prep and hiring, and come out for kickoffs or key moments.

Seattle, WA

Seattle is one of the strongest cloud and enterprise software markets in the country, shaped by the big tech companies headquartered in the region. Many Seattle startup founders came out of those companies, where they built great products but had large sales organizations doing the selling.

That's the gap. When you leave a company with a huge sales machine, you learn quickly that startups don't have one. Founder-led sales, first reps and early pipeline all have to be built from scratch.

A fractional VP of Sales builds it with you: ICP, outbound, discovery, pipeline stages and your first sales hires, sized for a startup rather than a big tech company.

I work with Seattle teams remotely week to week, which fits the region's hybrid culture, and travel for kickoffs and team sessions when being in the room matters.

Frequently Asked Questions