Fractional CRO · Advisor · GTM operator for VCs

You built the product. Now let's build the team that sells it.

I've worked every stage of the journey, from the first deal to $150M and an IPO. That's how I can tell you what's actually holding your revenue back, and plan the work to fix it and scale. Then I roll up my sleeves and do it with you.

Book a 30-minute call → Diagnose what's broken Plan the path to scale

The route we take together

01Why it mattersExperience you can’t fake
02DiagnoseFind what’s really broken
03Plan the workBuild it to last to year four
04How I workHands on, every week
05The resultRevenue you can plan on

01Why it matters

You can't advise on a journey you haven't made.

Anyone can install a CRM and hand you a playbook template. Knowing which problem to fix first, and what today's decisions will cost you at $20M or $100M, only comes from having lived it.

I help founders with the two hardest calls in sales: figuring out what's really wrong, and planning the work to scale.

02Diagnose the real issue

Your reps are missing their numbers. Is it them, you, or the product?

It's one of the most common things I hear from founders. You hired AEs, the pipeline looks busy, and the numbers aren't there. You suspect they aren't working hard enough, but without a sales background you can't tell for sure.

Guessing wrong is expensive. Fire good reps and you start over. Keep the wrong ones and you lose another year. I look at all three, and within 30 days you get a straight answer and a plan to fix it.

Is it the reps?

Effort and skill

Activity, pipeline coverage, and follow-through
Discovery, demos, and closing on real calls
Whether account loads are workable

Is it the leadership?

Setup and management

Hiring profile, ramp, and training
Quotas, comp, and whether targets are realistic
Coaching, inspection, and weekly cadence

Is it the product?

Market and message

Who is buying, and who should be
Positioning and pricing against the competition
Why deals are won and lost

03Plan the work to scale

What you do in year one decides what's possible in year four.

I know the pressure of a startup. You need revenue now, so you take shortcuts. Most of them work for a while. Then you try to scale, and every shortcut becomes a problem you have to unwind.

We move fast and build it right at the same time. That means training salespeople the right way and putting a foundation in place that holds up as the team grows from one rep to fifty.

Year 1 shortcut
Hire a "rockstar" AE and let them figure it out.

Year 4 problem
Every hire is a coin flip. Nobody can explain why one rep works and the next one doesn't.

How we build it
Hire to a defined profile and onboard every rep to the same written playbook.
Year 1 shortcut
Sell to anyone who will sign.

Year 4 problem
A customer base you can't serve well, high churn, and a roadmap pulled in ten directions.

How we build it
Define your ideal customer early, and walk away from deals that don't fit.
Year 1 shortcut
Keep pricing and discounts in the founder's head.

Year 4 problem
Every deal is a negotiation from scratch, and discounting becomes the culture.

How we build it
Set pricing, packaging, and discount rules your team can apply on its own.
Year 1 shortcut
Make up a comp plan for each new hire.

Year 4 problem
Unfair plans you can't change without losing your best people.

How we build it
One comp framework that scales from the first AE to the fiftieth.
Year 1 shortcut
Treat the CRM as an afterthought.

Year 4 problem
No data to forecast with, and a board that stops trusting your numbers.

How we build it
Clear stages, definitions, and a weekly forecast from the first deal.
Year 1 shortcut
Sink-or-swim onboarding.

Year 4 problem
Six-month ramps, missed quotas, and constant turnover.

How we build it
Structured training, call coaching, and certification before reps carry a number.

04How I work

I'm in the work, not watching from the outside.

You can build anything. Selling it is a different job, and most technical founders were never shown how. A slide deck of recommendations won't fix that.

So I take the seat next to you and do the work alongside you. You stay the captain. I put my hands on the controls of the revenue side, in real time, every week.

The deals

Join your sales calls and demos
Run discovery and handle objections with you
Build pricing and close the hard deals

The systems

Write the sales playbook from your real deals
Set up the pipeline, CRM, and stages
Run the weekly forecast and pipeline review

The team

Interview and hire your AEs and SDRs
Design comp plans and quotas
Train reps on a proven sales methodology
Coach and lead the reps day to day

05The result

From unpredictable spikes to a number you can plan around.

Before we started working together, a venture-backed B2B software company was booking anywhere from $20K to $75K in new ARR a month. Some months looked great. Others missed badly, and nobody could say which kind of month was coming.

Six months later, the team was booking more than $100K in new ARR every month, with the forecast landing within 5% of actual. The founder can plan hiring, spend, and the next raise around a number they trust.

Before working together$20K–$75KNew ARR a month, swinging month to month

After 6 months$100K+New ARR every month, consistently

Forecast accuracyWithin 5%Forecast vs. actual, month over month

$100K

$50K

BeforeAfter 6 months

Monthly new ARR, beforeAfter 6 monthsForecast for the month

Illustration of the pattern, not exact monthly figures.

What changed

Rebuilt the pipeline stages
Clear entry and exit criteria, so every deal's stage meant the same thing to everyone.
Fixed discovery
New questions built around finding real pain, not pitching features.
Ran structured trials
Defined success criteria and timelines up front, so trials ended in decisions.
Inspected deals weekly
Forecast calls that tested each deal's evidence, not the rep's optimism.

Founders I've worked with

In their words

Justin completely changed how I think about sales. At first, I was a bit intimidated by selling, but Justin broke it down into a clear, approachable process. He didn't just give advice, he rolled up his sleeves, coached me through real deals, and helped me build a repeatable sales motion that I'm using with AE's today. Thanks to his guidance, we closed our first major customers and have a real path to scale. I can't recommend him highly enough!

Jon FestejoCEO & Co-Founder, Salesbricks

Working with Justin has sharpened our entire approach - from how we position value to how we negotiate terms. He also played a key role in helping us successfully transition from a B2C motion to introducing a B2B sales process, giving us structure and confidence to go upmarket. We're now closing deals with far more consistency, and it's translated in stronger outcomes across the board.

Paulo GonzalezCEO & Co-Founder, Wellnite

"Justin has been a game-changer for our launch, accelerating our progress in way we didn't think possible. He's a trusted, strategic partner who brings clarity and momentum at every step."

Rocky PaapCEO, Feeynx.ai

"I feel really lucky to have learned from Justin, and I couldn't recommend him more. He sees 10 steps ahead and is able to help us prepare for what's next."

Jordan LeonardCOO & Co-Founder, LEOPARD.FYI

"Justin helps me with many GTM decisions. From taking calls with potential customers, interviewing AE candidates, and strategizing on pricing....he does it all!"

Amal Dar AzizCEO & Co-Founder, Maven, Inc.

"Justin is an exceptional GTM advisor who brings a rare ability to navigate both transactional, product-led growth motions and complex, enterprise deals. His guidance is consistently insightful, actionable, and grounded in real experience."

Burak AksarFounder, Spiky.ai

"I've been working with Justin for many years, and I continue to learn something new every time we connect. He's a pro when it comes to enterprise sales."

Nariman ShariatFounder, RolloutIQ

"We're not a traditional SaaS company, but Justin's knowledge and expertise in selling solutions and focusing on customer success is 100% relatable. He's a solid foundation of expert advice for any situation we encounter."

Ved RasicFounder & CEO, LeadDelta

Every engagement starts as a pilot

90 days to prove it works.

We agree on what success looks like up front and track it every week. By day 90 you have a written playbook, a working pipeline, a forecast you can trust, and a team trained to run it. All of it is yours to keep, and from there we decide together how far to fly.

Days 1–30 · Diagnose

Find what's actually working

Review every deal, call, and rep. Find out whether the gap is the team, the process, or the product. Build the first version of the playbook.

Days 31–60 · Build

Install the system

Stand up the process, CRM, and metrics. Run deals side by side with you. Tighten the pitch with every call.

Days 61–90 · Scale

Make it repeatable

Hire and train the team, set targets, and hand over a revenue engine built to scale, running on a weekly cadence instead of on heroics.

Fractional vs. full-time

You probably don't need a VP of Sales yet.

Hiring a full-time VP of Sales feels like the grown-up move. For most early-stage companies, it comes too soon and costs too much.

A fractional CRO builds the foundation first. When you're ready for a full-time leader, I help you hire the right one and hand them a sales engine that already works.

Full-time VP of Sales Fractional CRO

Timing

Most early-stage companies aren't ready for a VP. There's no repeatable motion yet and no team to lead.

Built for the stage you're at: finding the motion, writing the playbook, making the first hires.

Cost

A big base salary and equity, plus a search that can take six months before they start.

A fraction of the cost, and we can start within weeks.

Risk

First VP of Sales hires often don't last. A miss can cost you a year and a lot of equity.

Starts as a 90-day pilot with clear goals, so you see results before you commit further.

How they work

Many VPs expect a playbook and a team to already be in place. They manage, they don't build.

I build with you: the playbook, the pipeline, the hiring, and the training.

Incentives

Under pressure to show numbers fast, they often protect their seat instead of telling you hard truths.

No politics. I tell you what's really wrong, and my goal is a team that doesn't need me.

Ways to work together

Three seats. Same operator.

However we work together, you get someone who has been on the front lines: carried the number, built the team, and scaled it.

For founders building a team

Fractional CRO

I join your team and own the revenue function.

20–25 hours a week, in your Slack and on your calls
Owns pipeline, forecast, and sales hiring
Hires, trains, and coaches your reps directly

For founder-led sales

Front-line Advisor

Scaling sales takes advice from someone who has done it. Each week we work through your real deals, hires, and decisions.

Weekly working session on live deals and pipeline
A direct line when a deal can't wait

For venture firms

Portfolio GTM Operator

One hands-on operator across your portfolio, embedded with the companies that need it most.

Embedded support for priority companies
Workshops and office hours for the portfolio
Structured feedback to the GPs

How it works for VCs

Start with a 90-day pilot → A 30-minute call to see which seat fits.

About

Justin Roberts

I've spent my career on the front lines of sales at companies on their way to becoming category leaders.

I joined Salesforce early, with fewer than 1,000 employees, and spent five years seeing first-hand what a true rocket ship looks like. I saw it again at Box, which grew from about 40 employees to well over 1,000 while I was there. As a Sales Director, I helped take revenue from $3M to $150M and the company public.

At Lever, I took revenue from zero to $10M ahead of its $550M acquisition by Employ. As VP of Sales at SignalFx, I helped build the revenue org through its $1.05B acquisition by Splunk, then spent two years at Splunk on some of its largest enterprise observability deals. At Flatfile, I built revenue from zero to $5M.

Today I run Revenue Pilot, working with a small number of companies at a time so I can be fully in the seat with each one.

Connect on LinkedIn

From sales leaders I've worked with

"Can't think of a better coach than Justin Roberts for any founder who wants to evolve the way they engage in those critical conversations."

Jeremy KmetGM Americas, Notion

"Justin changed the trajectory of my professional career. He taught me that 'winning is contagious,' and this is a mantra that I'll continue to pass down to the teams that I'm fortunate to lead."

Mike BullardDirector of Sales, Ivo

"Justin was an incredible manager and I continue to learn something each time we connect. He taught me to foster a results-driven team environment, while developing the necessary skills to run a large sales org."

Sam SorboHead of Sales, Pulley

What it's like to work together

Hear it from Alex.

Alex is a technical founder with a great product and no idea how to sell it. Across 12 short episodes, you see what 90 days together actually look like: the first awkward calls, the blown meeting, the new playbook, and the team that runs it.

Alex is fictional, but each lesson comes from real founder scenarios.

Watch all 12 episodes →