JESSE KARKOUKLY
JESSE KARKOUKLY
Not Ready for a Head of Sales?
Not Ready for a Head of Sales?
Not Ready for a Head of Sales?
Good.
Good.
Good.
I help growing teams build revenue engines without the overhead.
I help growing teams build revenue engines without the overhead.
01. Set Your Team Up to Win
Hiring your first rep? Scaling a small team? I’ll help you move beyond founder-led sales by defining roles, setting comp, and designing a 30/60/90 plan that fits your stage. We’ll also run a live audit of your current pitch, pipeline, and sales activity so your team is set up to succeed.
01. Set Your Team Up to Win
Hiring your first rep? Scaling a small team? I’ll help you move beyond founder-led sales by defining roles, setting comp, and designing a 30/60/90 plan that fits your stage. We’ll also run a live audit of your current pitch, pipeline, and sales activity so your team is set up to succeed.
02. Build a Pipeline You Can Count On
Lead Generation is where most teams stall. It's the lifeblood of any successful revenue system. Scrappy outreach can only get you so far. I help you build a repeatable, ICP-driven system by combining outbound, referrals, and smart targeting so you can generate consistent, predictable qualified leads can actually close.
03. Deliver a Buyer Journey That Converts
Too many teams separate sales and marketing, then wonder why win rates struggle. I help you tighten your ICP, sharpen your message, and time it right across web, outbound, and live sales moments so the right people hear the right thing when it matters most. My team averages a 60% win rate on qualified deals.
02. Build a Pipeline You Can Count On
Lead Generation is where most teams stall. It's the lifeblood of any successful revenue system. Scrappy outreach can only get you so far. I help you build a repeatable, ICP-driven system by combining outbound, referrals, and smart targeting so you can generate consistent, predictable qualified leads that can actually close.
03. Deliver a Buyer Journey That Converts
Too many teams separate sales and marketing, then wonder why win rates struggle. I help you tighten your ICP, sharpen your message, and time it right across web, outbound, and live sales moments so the right people hear the right thing when it matters most.
04. Install Systems That Scale
Ditch the spreadsheet. When leads live in spreadsheets or scattered tools, deals slip. I’ll help you set up or optimize your CRM and pipeline to reflect your real sales process. Together, we’ll integrate automation, AI workflows, and sales tools that keep you focused on closing, not chasing.
04. Install Systems That Scale
Ditch the spreadsheet. When leads live in spreadsheets or scattered tools, deals slip. I’ll help you set up or optimize your CRM and pipeline to reflect your real sales process. Together, we’ll integrate automation, AI workflows, and sales tools that keep you focused on closing, not chasing.
Over the last decade in fast-paced tech, I’ve seen firsthand how sales teams get stuck: no systems, no visibility, and no real strategy - just good people grinding without results.
I started as the first sales hire at a startup and built the entire process from scratch, cold calls, door-to-door, handwritten pipeline. That team scaled from 5 to 200, and we closed a $60M Series B.
I continued my path in the startup space where I evolved my skillset to focus on systems, launching new functions, and building revenue engines on winning teams. Today, I work with founders and operators to apply those same principles - helping them build what lasts.
Over the last decade in fast-paced tech, I’ve seen firsthand how sales teams get stuck: no systems, no visibility, and no real strategy - just good people grinding without results.
I started as the first sales hire at a startup and built the entire process from scratch, cold calls, door-to-door, handwritten pipeline. That team scaled from 5 to 200, and we closed a $60M Series B.
I continued my path in the startup space where I evolved my skillset to focus on systems, launching new functions, and building revenue engines on winning teams. Today, I work with founders and operators to apply those same principles - helping them build what lasts.
Carly L.
Carly L.
Account Executive
"One of the most people-focused managers I’ve ever worked with. Jesse coached with care, drove new revenue with precision, and kept the whole team aligned and motivated."
"One of the most people-focused managers I’ve ever worked with. Jesse coached with care, drove new revenue with precision, and kept the whole team aligned and motivated."
Michelle E.
Michelle E.
Head of Operations
"Jesse balances strategy with execution like few others. He’s the person I’d want in the room when solving hard problems — motivating, grounded, and always thinking big. I’d trust him with my business, my team, even my kids."
"Jesse balances strategy with execution like few others. He’s the person I’d want in the room when solving hard problems — motivating, grounded, and always thinking big. I’d trust him with my business, my team, even my kids."
Nicole B.
Nicole B.
Director of Partnerships
"Jesse consistently landed high-value clients and cross-sold seamlessly. He brought energy, professionalism, and strategy to every deal. Working with him made our team stronger - and a lot more fun."
"Jesse consistently landed high-value clients and cross-sold seamlessly. He brought energy, professionalism, and strategy to every deal. Working with him made our team stronger - and a lot more fun."
F A Q
How do we actually build a sales engine?
What kinds of businesses do you work with?
We already have a sales team, where do you fit in?
Is this fractional sales leadership?
What metrics should we actually track?
How do we actually build a sales engine?
What kinds of businesses do you work with?
We already have a sales team, where do you fit in?
Is this fractional sales leadership?
What metrics should we actually track?
Or just reach out! - I’d love to hear from you.
Or just reach out! - I’d love to hear from you.
Say Hello
Say Hello