4.5X REVENUE GROWTH
IN 12 MONTHS
FROM FOUNDER-LED SELLING TO A SCALABLE REVENUE ENGINE
When I began working with AccountAim, revenue relied heavily on founder intuition and bespoke conversations. Every opportunity felt critical. Qualification lacked consistency. Growth depended more on effort than structure.
Over the next 12 months, we built a disciplined, repeatable sales motion designed to scale.
✔ Standardized sales process
✔ Dramatically higher conversion rates
✔ Faster, more confident decision making
✔ Clear qualification discipline
✔ A foundation built for scale
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Revenue stopped being reactive.
It became architected.
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“This gave me reassurance and a true thought partner from the earliest days of finding product market fit to scaling our processes and team.”​
Josh McClanahan
Co-Founder & CEO, AccountAim
SENIOR SALES LEADERSHIP. WITHOUT THE FULL-TIME COST.
I embed with B2B companies, Series A founders and PE-backed operators as a Fractional VP of Sales.
I build the structure, lead the team, and drive revenue. No ramp time. Just results.
I'm Lester Sydney.
I've been in the seat you're in right now.
I stepped out of sales to run a company. The pressure was real. The decisions mattered. And I learned firsthand what it costs to be accountable for revenue without a clear system to support it.
That experience changed everything about how I see sales leadership.
Most companies don't have a talent problem. They have a structure problem capable leaders being asked to hit targets without the process, pipeline discipline, or sales infrastructure to make it repeatable.
That's exactly what I build.
As your Fractional VP of Sales, I come in as a senior operator not an advisor on the sidelines. I work alongside your team, install a system that runs without your constant involvement, and stay until the revenue engine holds on its own.
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​​​WHAT I BRING​
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Closed complex, multi-stakeholder, seven-figure deals with Fortune 500 and Global 2000 companies — Citigroup, Home Depot, Freddie Mac, Dell, IBM, DigitalOcean, and Johnson & Johnson
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Consistent top performer across multiple organizations and market cycles
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Built and led sales teams from early-stage through growth — as both a player and a coach
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Operated as CEO, accountable for revenue, hiring, and P&L — I understand the full business, not just the sales function
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Advised founders and PE-backed operators on GTM strategy, sales hiring, and revenue architecture
HOW I SUPPORT COMPANIES
This isn't advisory work from a distance.
I embed directly into your business as a Fractional VP of Sales with skin in the game and a seat at the table. I own the sales motion alongside you, not above you.
Whether you're a Series A founder who needs to stop being the only person who can close, or a PE-backed operator with a team that isn't hitting its number. I come in, diagnose what's broken, and build what's missing.
The result: a sales function that runs with structure, accountability, and predictability. Without requiring your constant involvement.
FRACTIONAL VP OF SALES
THE PROBLEM​ You need senior sales leadership but a full-time VP hire is premature, expensive, or both. In the meantime, deals are stalling, pipeline is unclear, and the team lacks direction.​​
THE SOLUTION I step in as your VP of Sales on a fractional basis. I set the strategy, run the cadence, coach the team, and drive the deals. You get a seasoned operator without the full-time overhead and a sales motion built to outlast my engagement.
BUILDING SALES FUNCTION
PROBLEM​ Most companies hire salespeople before they build the system. That creates inconsistency, unreliable pipeline, missed targets, and frustrated reps who don't know why deals stall.​​
THE SOLUTION I build the infrastructure your team runs on discovery framework, pipeline stages, qualification discipline, forecasting cadence, and playbook. Sales stops being reactive and becomes repeatable.
TEAM PERFORMANCE & DEAL STRATEGY
PROBLEM: Your team is working hard but the numbers aren't there. Deals stall late. Forecasts are wrong. Objections go unhandled. No one has a shared language for why opportunities move or don't.
THE SOLUTION I work directly with your team on live deals call reviews, deal strategy, objection handling, and access to decision-makers. Every session is grounded in what's in your pipeline right now, not hypotheticals.
FOUNDER REFLECTIONS
Pattern I See Repeatedly
WHY I DO THIS WORK
I've operated at the board level and inside the day-to-day reality of sales; Carrying a number, building teams, and being accountable for revenue when the margin for error was zero.
Most companies don't stall because the people aren't capable.
They stall because no one has installed the infrastructure that makes capability repeatable. Pipeline is unreliable. Deals stall for reasons no one can articulate. The forecast is a guess dressed up as a number. And the founder or operator ends up back inside every deal; not because they want to be, but because nothing holds without them.
That's not a people problem. That's a missing sales function.
Every quarter without a real system is a quarter of compounding cost; lost deals, wrong hires, and leadership bandwidth spent on work that should be running without you.
That's the problem I fix.
I come in as an embedded operator; not an advisor on the sidelines and build the sales motion, lead the team, and install the infrastructure that lets your business grow without depending on any one person to hold it together.
THE
OUTCOME
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Your sales function runs on a clear system not on founder involvement or individual heroics
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Pipeline reflects reality and your forecast becomes something leadership can act on
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Your team operates from a shared process; same qualification, same discovery, same standards across every rep
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Deals advance because of structure, not because the right person happened to be in the room
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You get your time back to focus on the work only you can do; product, team, and the decisions that actually move the company forward
“Most founders don’t struggle because they’re bad at sales. They struggle because they’ve never been given a clear way to think about sales yet the business depends on it working.”
Sales rarely fails due to lack of effort. It fails when leaders are forced to make decisions without a framework for how sales actually operates. Once founders have a mental model they trust, execution becomes far simpler.
Sean Woods
CEO
CGM Sports
Lester helped bring structure and momentum to our strategy at a pivotal stage of our business. His guidance during a high-stakes negotiation with a high-profile athlete was decisive, and his ability to identify what actually mattered saved us time, uncertainty, and costly missteps. If you’re looking for someone who moves conversations to decisions, Lester does exactly that.
James Geyer
Co-Founder & COO
AccountAim
Lester played a key role in shaping AccountAim’s go-to-market strategy. His ability to combine hands-on sales coaching with a clear understanding of early-stage execution had a measurable impact on our traction and momentum.
Devdut Dala Founder
MittiLabs
Since working with Lester, we’ve seen a significant improvement in our sales results. He unlocked an entirely new perspective—not just on how to approach sales, but on how to communicate more effectively and have more meaningful conversations with prospects and customers.
Ryan Hetrick
Founder & CTO
CGM Sports
Lester has been an incredible mentor and asset for us at CGM Sports as he continually pushes us to be the best version of ourselves. Lester has been selfless and is willing to help us work through our company's most difficult problems. He is always willing to go the extra mile for us and has helped me progress as an entrepreneur and leader.
SALES PERFORMANCE & EXECUTIVE MINDSET
SALES MINDSET COACHING
At a certain level, the gap is almost never technical.
After 18 years closing seven-figure deals, building teams, and operating as a CEO — I've seen this pattern repeatedly: the people who plateau aren't lacking skill. They're running into something internal that their external performance has finally caught up to.
Hesitation before hard conversations. Confidence that rises and falls with the pipeline. Discipline that erodes when momentum slows. Decisions that carry the weight of the last deal into the next one.
These patterns are expensive. And they compound quietly.
This is 1:1 performance work for founders carrying revenue pressure, sales leaders accountable for team results, and senior sellers who know they're capable of more. It's direct, practical, and grounded in what's actually happening in your professional life right now.
Not motivational. Not theoretical. Internal calibration under real pressure.
WHAT WE WORK ON
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Identifying the specific patterns that show up when pressure increases and dismantling them before they cost deals
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Building self-awareness around avoidance, over-preparation, and the behaviors that masquerade as productivity
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Reframing pressure so it sharpens decision-making instead of distorting it
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Restoring the confidence and discipline that made you effective and making it independent of short-term results
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Building a sustainable internal foundation that performs when the quarter is behind, the deal stalls, and the stakes are real
WHO THIS IS FOR
Founders, sales leaders, and senior individual contributors who are performing below what they know they're capable of and recognize the gap isn't skill.
Chris Cooper
Sr. Director Sales
Working with Lester was critical to my transition into B2B sales. He helped me develop a repeatable framework that enabled me to thrive as an Account Executive. That foundation led to a promotion into sales leadership, where I now train and develop a team using the same principles.
Joseph Krikorian
Sr. BDBR
Lester is an empathetic and highly self-reflective leader who finds genuine fulfillment in helping others succeed. In just one year, I learned more about sales from Lester than I had in several years of my professional career. He has been far more than a sales mentor—his impact has been both personal and professional.
Chris Collard
Biz Dev Director
Lester’s coaching had an immediate positive impact and helped me take greater ownership of my career. I value his direct communication style, high level of professionalism, and the depth of real-world experience he brings to every conversation. Under his mentorship, I continue to improve both personally and professionally.
Ronsan Mendoza
Financial Advisor
Three words describe the impact of Lester’s mentorship: valuable, authentic, and life-changing. Learning from his experience and expertise has helped me grow not just professionally, but as a person.