EXPERIENCE
I’m Lester Sydney.
I help startup founders and CEOs who are new to sales leadership get time back, avoid costly mistakes, and lead sales with confidence.
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My consulting delivers clear frameworks and grounded mindset shifts so sales works without becoming your full-time job.
I’ve been in that seat.
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I stepped out of sales to run a company without the structure I was used to. The pressure was real. The decisions mattered. I learned what it feels like to be accountable for outcomes without a clear way to think about sales.
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That experience changed how I see sales leadership.
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Since then, I’ve carried a number, led enterprise deals, built teams, and seen what breaks and what holds when pressure shows up.
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What I see most often isn’t a capability issue.
It’s capable leaders being asked to run sales while building a company, without structure or support.
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That’s the problem I help solve.
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A few things I've done​
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Closed complex, multi-stakeholder, seven-figure deals with Fortune 500 and Global 2000:
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Citigroup, Home Depot, FreddieMac, Dell, IBM and Johnson & Johnson.
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Repeated top performer ​
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Led sales teams across growth stages
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Served as CEO, accountable for revenue, hiring, and P&L
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Advised founders and CEOs on Sales and GTM decisions
HOW I SUPPORT FOUNDERS
My work is designed for startup founders and CEOs who are responsible for sales for the first time build a sales function that delivers results without requiring their constant time and attention.
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I provide a practical sounding board for the sales decisions you’re facing in real time from discovery and deal progression to proof of concept and forecasting. Together, we put structure around how deals move so progress is clear and repeatable.
Ambiguity is removed from pipeline, stages, and next steps. Sales becomes something you can lead with confidence instead of manage by instinct.
The result is momentum without founder dependency.
FOUNDER & CEO ADVISORY
PROBLEM​ Founders face new sales challenges every day pricing decisions, deal stalls, unclear pipeline, and hiring calls they’ve never had to make before.​​
THE SOLUTION A weekly operating rhythm with a trusted partner to clarify decisions, translate strategy into execution, and keep sales focused on what actually moves revenue.
BUILDING SALES FUNCTION
PROBLEM​ Most startups hire sales before they build the system.That creates inconsistency, unreliable pipeline, and wasted effort.​​
THE SOLUTION Putting structure around discovery, proof of concept, and deal stages so pipeline becomes predictable.
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TEAM WORKING SESSIONS
PROBLEM: Teams don’t fail from lack of effort, they fail when there’s no shared system for discovery, objection handling, access to decision-makers, or accurate forecasting.
THE SOLUTION Establish a standardized discovery framework, conduct weekly call and deal reviews, formalize objection handling through a shared playbook, and apply clear strategy and tactics to advance and win active opportunities.​
FOUNDER REFLECTIONS
Pattern I See Repeatedly
WHY I DO THIS WORK
I’ve advised founders and CEOs at the board level and inside the day-to-day reality of sales and go-to-market execution.
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Most growth doesn’t stall because founders aren’t capable or committed.
It stalls because sales becomes a time sink decisions take longer than they should, execution lacks structure, and progress depends too heavily on the founder.
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That's an expensive problem.
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Every hour spent figuring out sales is an hour not spent improving the product, strengthening the team, or building the business only a founder can build.
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That’s where I come in.
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I help founders put a clear, repeatable sales framework and operating structure in place with discipline and direction without requiring constant founder intervention.
THE
OUTCOME
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You get your time back to focus on product direction, leading your team, and doing the work only you can do.
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You stop spending hours figuring out sales.
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Your team operates from a clear structure instead of intuition.
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Progress no longer depends on your constant involvement.
“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.
1:1 SALES COACHING
SALES MINDSET COACHING
Sales isn’t a talent problem.
It’s a mindset problem.
After 18 years in sales through wins, losses, burnouts, and rebuilds I’ve learned this firsthand: the difference between people who grow and people who stall isn’t effort or intelligence. It’s how they think when things get hard.
Slumps happen. Confidence dips. Momentum disappears.
Most people either push harder without clarity or quietly lose belief.
I help you build the internal framework to stay grounded, focused, and effective when results aren’t cooperating.
This is not motivational talk.
It’s practical mindset work rooted in real sales pressure.
WHAT WE WORK ON
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Identifying and dismantling self-limiting beliefs that show up in deals, conversations, and decision-making
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Building self-awareness around patterns that create stalls or avoidance
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Reframing pressure so it sharpens performance instead of draining it
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Restoring confidence, discipline, and emotional control during downturns
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Creating sustainable motivation that doesn’t depend on short-term wins
WHO THIS IS FOR
Sales professionals who know they’re capable of more but feel stuck, inconsistent, or mentally fatigued by the grind.
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.