Fleetmatics ($2.6B) · Whip Around ($100M)
Michael Flournoy

Michael Flournoy

Fractional VP of Sales for B2B SaaS

First employee at Whip Around. Helped build it to a $100M acquisition.

Before that, I was inside Fleetmatics through its $2.6B sale to Verizon. Now I bring that playbook to a small number of B2B SaaS founders at $1M–$10M ARR who need a sales engine that runs without them.

Book a Free 30-Min Call → Get the Free Playbook

30 minutes · No pitch · I’ll tell you if I’m not the right fit

Michael Flournoy

Michael Flournoy

Founder, GSD Associates · CCO, QuickManage

What you get on the free call:

  • ✓ 30 minutes, no pitch
  • ✓ I’ll find your biggest sales bottleneck
  • ✓ 3 specific actions you can take this week
  • ✓ A straight answer on whether you need me
Book Your Free 30-Min Call →
Pick a time that works · 30 min · No pitch
Full disclosure: I’m Chief Commercial Officer at QuickManage, a fleet TMS I first worked with as a fractional VP. I keep a short list of founder clients alongside it, so every engagement gets my direct attention.
$2.6B
Fleetmatics, acquired by Verizon
$100M
Whip Around acquisition. I was the first employee.
Month 1
Demos and discovery rebuilt at QuickManage
$1M–$10M
The ARR range I work with
The real problem

Your pipeline isn’t broken.
Your process is.

Most founder-led sales teams don’t have a people problem. They have a process problem. If two or more of these sound familiar, you’re leaving revenue on the table.

No clear ICP

Reps chase anyone who says yes and burn weeks on deals that were never going to close.

Everyone qualifies differently

One rep’s “qualified” is another rep’s “maybe someday.” Your forecast is a guess.

Long cycles, low conversion

Deals drag for months and nobody can say why you win or why you lose.

The founder is still the closer

Every big deal runs through you. That’s not a sales team. That’s a bottleneck with a CRM.

What I fix in the first 30 days

Define your real ICPWho actually buys, why they buy, and who to stop chasing.
Build a qualification frameworkClear rules so every rep qualifies the same way.
Rebuild discovery and demosReplace vague questions with must-ask criteria that move deals forward.
Install the scoreboardActivity → meetings → pipeline → revenue, tracked weekly.
Find Your Bottleneck: Book a Free Call →

Three Ways to Work With Me

Pick the depth you need. Every engagement is built around one outcome: a repeatable sales engine your team can run.

Sales Consulting

Build pipeline, refine process, align your tech stack

  • Inbound lead handling: Speed-to-lead, routing, qualification, SLAs
  • Outbound engine: Targeting, messaging, sequences, meeting conversion
  • KPI clarity: Activity → Meetings → Pipeline → Revenue

Best for:

Founder-led teams building their first repeatable process

Learn more · From $4K/mo →
MOST POPULAR

Fractional VP of Sales

Senior leadership embedded for 3-6 months

  • SDR/BDR systems: Weekly targets, coaching cadence, QA process
  • SDR→AE handoff: Clear rules, definitions of qualified, no more dead leads
  • Deal review & coaching: Discovery frameworks to lift conversion

Best for:

SaaS founders at $1M–$10M ARR with no sales leader, or one who needs backup

Learn more · $6K–$10K/mo →

Sales Process Development

Define ICP, shorten cycle, improve conversion

  • Discovery framework: Qualification checklist, must-have questions
  • Stage definitions: Exit criteria to stop stalled pipeline
  • Follow-up standards: Handoff notes requirements (no more thin opps)

Best for:

Teams with reps but no shared playbook

Learn more · From $5K →
Full-time VP of SalesFractional VP (me)
Cost$200K+ salary, plus equity$6K–$10K / month
Time to start6–12 month search2–3 weeks
Track recordUnknown until they’re in the seatTwo exits: $100M and $2.6B
Schedule Your Free Strategy Call

30-minute call · No obligation · Straight answers

How an Engagement Runs

From diagnosis to a sales engine that runs without you.

1

Discovery & Diagnostic (Week 1-2)

Deep dive into your current state—pipeline analysis, rep shadowing, tech stack audit, ICP refinement. I find the bottlenecks killing your conversion.

Pipeline Audit Rep Shadowing ICP Analysis
2

Framework & Playbook Build (Week 3-4)

Create your sales playbook—discovery framework, qualification criteria, stage definitions, handoff protocols. Everything documented and repeatable.

Discovery Framework Qualification Checklist Stage Definitions
3

Training & Rollout (Week 5-6)

Train your team on the new frameworks. Weekly coaching sessions, live deal reviews, and QA calls to ensure adoption and correct execution.

Team Training Deal Reviews Live Coaching
4

Optimization & Scale (Month 2-6)

Iterate based on data. Refine messaging, optimize sequences, improve conversion points. The end state: a machine that runs without you micromanaging it.

Data Analysis Message Testing Conversion Optimization
Track record

Three fleet SaaS companies.
One playbook.

I’ve built sales in this world from the first hire to the exit. Here’s where the playbook comes from.

Whip Around · Fleet inspection SaaS
$100M acquisition

First employee. Helped open the US office with a team of four and built the sales engine from scratch: the ICP, the process, and the team.

Read the case study →
Fleetmatics · Fleet management SaaS
$2.6B Verizon exit

Inside a high-growth sales org as it went public and sold to Verizon. That’s where I learned what sales discipline looks like at scale.

QuickManage · Fleet & transportation TMS
Fractional VP → CCO

Came in as fractional VP of Sales and rebuilt how the team runs demos and discovery in month one. Today I’m their Chief Commercial Officer.

Read the case study →
Why founders work with me

An operator, not a consultant.

I’ve carried the bag

I’ve sold, hired, coached, and built the process myself. You get what worked in the field, not theory from a slide deck.

I know vertical SaaS

Fleet, transportation, and other vertical markets have long cycles and skeptical buyers. I’ve sold into them for years.

I build it, then hand it over

Everything is documented and owned by your team. The goal is a sales engine that runs without me, and without you in every deal.

I’ll tell you if you don’t need me

If a $199 audit or a playbook will solve it, that’s what I’ll recommend. I keep my client list short on purpose.

Not ready for a call?

Start on your own.

Three self-serve ways to fix your sales process. No call required.

Sales Audit · One-time
$199

A custom 10-page audit of your sales process with your 3 biggest bottlenecks and a 30-day action plan. Delivered in 48 hours.

See what’s included →
30-Day Sales Sprint · Cohort
$999 / 4 weeks

A live 4-week cohort with up to 15 founders. Includes the audit, 12 hours of group coaching, and a 1-on-1 call with me.

See the next cohort →
Sales OS · Monthly
$47 / month

Templates, discovery scripts, rep scorecards, a founder Slack community, and monthly office hours. Cancel anytime.

See what’s included →

Or start free: The 0-to-$100M Sales Playbook, 7 lessons from building Whip Around’s sales engine.

Common Questions

How is fractional different from hiring a full-time VP of Sales?

What size companies do you work with?

You're CCO at QuickManage. Do you have time for clients?

How long does an engagement last?

What if we already have a sales leader?

What happens on the free call?

Ready to Build a Sales Engine That Scales?

Book a free 30-minute call. We’ll look at where your deals stall, and you’ll leave with three things to fix this week. If I’m not the right fit, I’ll tell you.

30-Minute Call

Quick but thorough

Tailored Insights

Specific to your situation

No Obligation

Straight answers

Book Your Free Strategy Call Now

30 minutes · No pitch · Three actions you can use this week