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Get a VP of Sales Who's Actually Done It.

Senior sales leadership embedded in your team for 3–6 months. Same playbook that scaled Whip Around to $100M and Fleetmatics to $2.6B.

Build the system. Coach the team. Own the number. No $200K full-time hire needed.

🏆 Whip Around $100M
🏆 Fleetmatics $2.6B
Book a Free Strategy Call → See Pricing

💪 30-day proof-of-value · ⚡ Results in 30 days · 📉 this month days left in this month to book

Michael Flournoy

Michael Flournoy

Your Fractional VP · Whip Around ($100M) · Fleetmatics ($2.6B)

$6K–$10K/mo
vs. $200K+ full-time VP
✓
Embedded 1-2 days/week
✓
Weekly pipeline review + rep coaching
✓
Build sales process, systems, playbooks
✓
Own the number, coach through it
Book Free Strategy Call →

30-min call · No pitch · We tell you if we're not the fit

$100M
Acquisition — Whip Around
0→1
US office built from scratch
30 Days
To measurable results
$1M–$10M
ARR sweet spot

What's Included

Everything a VP of Sales does — minus the $200K salary, equity, and 6-month onboarding.

SDR/BDR System Build

Weekly targets, coaching cadence, QA process. Your outbound engine runs on a repeatable system — not hustle and hope.

Weekly activity targets by rep
1:1 coaching cadence + call reviews
QA process for messaging quality

SDR → AE Handoff Rules

Clear definitions of "qualified." No more dead leads clogging your pipeline. No more AEs wasting time on tire-kickers.

Written qualification criteria (BANT/MEDDIC)
Handoff scorecard and acceptance rules
CRM stage gates enforced

Deal Review & Coaching

Weekly pipeline reviews. Discovery frameworks to lift conversion. Your AEs close more because they're coached like pros.

Weekly deal review with each AE
Discovery call framework + live coaching
Win/loss debrief process

Forecasting & Pipeline Accountability

Weekly forecast calls. Pipeline reviewed with the same rigor a board expects. You'll always know where the quarter is heading.

Weekly pipeline review + forecast report
CRM hygiene enforcement
Monthly exec summary for leadership

Also included in every engagement:

Sales playbook (written, usable)
Comp plan review & recommendations
Hiring profile if you need to add reps
Tech stack audit (CRM, sequencing)
ICP refinement workshop
Direct Slack/email access to Michael

How It Works

Three phases. Each one builds on the last.

1

Weeks 1–2: Diagnostic

We audit your current state — pipeline, team, process, CRM, messaging, comp. No guesswork. We find exactly where revenue is leaking.

Deliverable: Written diagnostic report + priority action list

2

Weeks 3–8: Build & Embed

We fix the leaks. SDR system, handoff rules, deal coaching, forecast cadence. Michael is in your weekly calls, working alongside your team.

Deliverable: Running systems, coached team, clean pipeline

3

Month 3–6: Scale & Handoff

The system runs itself. We document everything so it outlasts the engagement — playbook, processes, hiring profile if needed. You own it when we're done.

Deliverable: Full sales playbook + transition plan

Pricing

A full-time VP of Sales costs $180K–$250K/year in salary alone — before equity, benefits, and a 4-6 month ramp. This is a fraction of that.

Starter

For founders testing fractional leadership

$6K /month
  • Up to 2 days/week embedded
  • Weekly pipeline review
  • SDR/AE coaching cadence
  • Diagnostic + playbook
  • Slack/email access
Book a Call
Most Popular

Full Engagement

For companies serious about building the machine

$8K /month
  • Up to 3 days/week embedded
  • Full SDR/BDR system build
  • Weekly deal review + coaching
  • Forecasting & pipeline accountability
  • Comp plan + hiring profile
  • Tech stack audit (CRM/sequencing)
  • Full sales playbook on exit
Book a Call

Strategic

For high-growth companies scaling fast

$10K /month
  • Full-time equivalent availability
  • Everything in Full Engagement
  • Board/investor reporting support
  • Active hiring & interview support
  • Channel/partnership strategy
Book a Call

Minimum 3-month engagement. Month-to-month after that. No long-term lock-in.

Best For:

Mid-market B2B companies with 5–20 person sales teams

You're stuck at $1M–$10M ARR and can't figure out why growth stalled
Sales is still founder-led — you're in every deal and it's not scalable
You have reps but no system — results are inconsistent rep to rep
You can't justify a $200K VP of Sales hire yet
You need results in 30–60 days, not 6 months of onboarding

The Whip Around Story

This isn't theory. Michael was one of 4 people who opened the US office of Whip Around — a fleet management SaaS — and built the sales engine from scratch.

0 customers. 0 process. 0 playbook. They built it all and grew the company to a $100M acquisition.

That's not a resume bullet. That's the exact playbook we bring to your company.

Read Michael's full story →
💼 Audit
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Other Services

Sales Consulting

Build pipeline, refine process, align your tech stack. Best for growing companies building their first scalable sales process.

Learn more →

Sales Process Development

Define ICP, shorten cycle, improve conversion. Best for established B2B companies refining their growth engine.

Learn more →

Common Questions

A consultant gives you a deck and a list of recommendations. A Fractional VP shows up in your team's calls, coaches your reps live, runs your pipeline reviews, and is accountable to the same number you're accountable to. We're embedded, not advisory.
Most clients see measurable process improvements within 30 days. Meaningful pipeline impact typically shows up in 60–90 days, depending on your sales cycle length. We'll set clear KPIs in week one so you know exactly what "working" looks like.
Yes, but capacity is intentionally limited. GSD Associates works with a maximum of 4–5 clients at any given time to ensure every client gets real attention — not a templated playbook. Spots fill up. If you're interested, don't wait.
Primary expertise is in fleet/transportation SaaS and B2B SaaS broadly. The frameworks apply across industries — but if you're in fleet, logistics, or transportation tech, Michael has been in your buyers' shoes and knows your sales cycles cold.
3 months minimum. Real results take time to build — anyone promising a transformation in 30 days is selling you something. After the initial 3 months, we go month-to-month with 30 days notice to exit on either side.
30 minutes. No pitch deck. We talk about where you are, where you're stuck, and whether we're the right fit. If we are, we'll talk next steps. If we're not, we'll tell you honestly and point you in the right direction.

Ready to stop guessing?

Book a free 30-minute strategy call. We'll look at your pipeline, your team, and your process — and tell you exactly where the problem is.

Book Your Free Strategy Call

No commitment. No pitch. Just a real conversation.