Hilton Head Island, South Carolina
I build revenue engines that last.
Twenty years in revenue strategy and business operations, shaped at Kellogg and in the rooms that followed. I've seen the wins and the losses, and I've learned from some of the best leaders and companies in business. Now I build AI operating systems that give revenue teams capacity: the weekly groundwork across sales, operations and finance runs on agents, and people stay on the relationships and decisions.
[PROOF LINE: Keith to approve metrics]
What I do now
Full time
SVP, Sales and Partnerships
I lead sales and partnerships for a team building a better way for school districts to manage their special education programs and IEP-related services. We build capacity and operational effectiveness, using virtual services and technology to make the most of district resources and meet students where they are.
I came in as an advisor in 2025 to build the commercial plan. In January 2026 that work became this seat.
huddleupcare.comSelect engagements
Revenue strategy for leadership teams
I take on a small number of advisory and fractional CRO engagements with leadership teams who want to build the revenue engine: strategy, process, team, pipeline, forecasting, and putting AI to work across all of it.
Some start as a focused diagnostic and grow into deeper work. If the revenue engine is what stands between your team and the next stage, I am glad to have that conversation.
You can also email me at keith@kdk711.com or find me on LinkedIn.
Want to know more about the AI practice? Visit sidekickoffice.com.
My AI practice
Founder, The sideKick Group
sideKick builds AI operating systems and capacity installs for small and mid-size businesses around Hilton Head, Bluffton, Charleston and Savannah. We set them up on the tools a business already pays for and stay until their people run them. Nothing goes out without a person approving it.
It is where I build and teach the AI side of my work, close to home. What I learn there makes me a better revenue leader, and the reverse is just as true.
sidekickoffice.comMy story
I started in the engine room. At SchoolNet, a venture-backed education company in New York, I ran sales operations and built the pipeline, CRM, forecasting, pricing, territory and comp systems. Those systems carried the company all the way through its acquisition by Pearson.
Then I spent years on the other side of the machine, carrying the number it produces. I was an account general manager at Pearson, led customer success at ThinkCERCA and enterprise partnerships at Discovery Education, and ran enterprise sales for LEGO Education in North America, where we moved the business from channel sales to direct. As CEO of Curriki I moved the organization onto an open-source SaaS platform. At pi-top, as global vice president of sales and revenue operations, I helped take a retail business into B2B education.
Kellogg gave me the systems lens. The jobs taught me what happens when those systems meet a real number.
I have sat in nearly every seat a revenue organization has. I have been the rep whose territory was drawn badly, the sales leader whose forecast was built on hope, and the CEO who needed the number to be true. Those seats taught me that growth runs on the same foundation everywhere. The buyer has to understand the message. The team has to know the process. The data has to be clean, and finance has to trust the forecast. When marketing, sales and customer success pull toward one number, the business grows. When they don't, it leaks.
In 2021 I started The sideKick Group to do that work alongside other leadership teams: sales process, forecasting, comp and CRM, for CEOs and investors who needed the revenue engine to run cleaner. Along the way I built the revenue operations function at Carnegie Learning, a PE-owned learning company. In 2025 one advisory engagement brought me to Huddle Up Care. I believed in the work and the mission enough to stay, and since January 2026 I have been there full time. I still take on select advisory and fractional CRO work alongside it.
Why AI, and why now
Technology was always part of how I saw the edge. At Kellogg I noticed there were strong practitioners everywhere. What was thinner was a real understanding of how technology could add hours and clarity across a whole business, not just inside one department. For years that view had nowhere to go. Agents changed that.
As a Claude for Small Business trainer and an expert user of tools like Grok Bot, Claude Code and Perplexity, I deploy agentic operating systems for businesses. I've invested deeply in these technologies, and I have a full grasp of the impact they can have on a business.
In my advisory engagements and at sideKick, those agents take on the weekly groundwork across sales, operations and finance, so teams gain capacity, the business runs leaner, and people spend their time on relationships and decisions.
I treat AI as a tool inside sound management, not a substitute for it. Point it at a named job, measure what it gives back, and keep a person on anything that goes out the door. I do the dirty work on the front end of the technology so the people I work with don't have to.
How I work
Look at what the data says before you pick the story. Hope is not a forecast.
Most teams do not need another system. They need hours back on the ones they already pay for. A tool nobody runs just adds noise.
I will not treat the last ten years as a mistake. You made those calls with what you had in front of you. Then we fix what is leaking.
If it only works when I am in the room, I did it wrong. The goal is a team that owns the system.
Where I've led
MBA, Kellogg School of Management, Northwestern University. BS in Marketing Management, Providence College, where I played Division I soccer.
Outside work, I am a father of three daughters and coach a girls' soccer team. I have run six marathons for pediatric cancer research at Memorial Sloan Kettering, and I am a board member of Fighting Pretty, a nonprofit that supports women facing cancer.
What shapes my thinking
Find the constraint. Everything else waits on it.
Face the brutal facts before you choose the story.
Pick a pace you can hold in good years and bad. Then hold it.
If the room cannot say why it matters, the plan will not survive contact.
Strategy is choosing what not to do. Name the tradeoff out loud.
Make it about the other person. Ask, then listen.
Your output is the output of the people you influence.
Fix the loop, not the symptom you noticed first.
Good companies miss the next curve by protecting the current one.
Build while cash and doubt are loud. Keep the next step concrete.
Questions
Keith Kostrzewski is a revenue leader who builds the whole engine: the strategy, the sales process, the team, the pipeline and the forecast, with marketing and customer success pulling toward the same number. He started in sales operations at SchoolNet, ran enterprise sales for LEGO Education in North America, served as CEO of Curriki, and was global vice president of sales and revenue operations at pi-top. Today he is SVP, Sales and Partnerships at Huddle Up Care.
Yes. Keith takes on a small number of advisory and fractional CRO engagements with leadership teams who want to build the revenue engine: strategy, process, team, pipeline, forecasting, and putting AI to work across all of it. Some start as a focused diagnostic and grow into deeper work. The simplest way to start is a 30-minute conversation, or an email to keith@kdk711.com.
Keith is a Claude for Small Business trainer and an expert user of tools like Grok Bot, Claude Code and Perplexity. He deploys agentic operating systems that take on the weekly groundwork across sales, operations and finance, so teams gain capacity and people spend their time on relationships and decisions. He treats AI as a tool inside sound management: point it at a named job, measure what it gives back, and keep a person on anything that goes out the door.
sideKick, The sideKick Group, is the AI practice Keith founded and where he builds and teaches the AI side of his work. It builds AI operating systems and capacity installs for small and mid-size businesses around Hilton Head, Bluffton, Charleston and Savannah, set up on the tools they already pay for, and stays until their own people run them. Nothing goes out without a person approving it. More at sidekickoffice.com.
Keith lives on Hilton Head Island, South Carolina. He holds an MBA from the Kellogg School of Management at Northwestern University and a BS in Marketing Management from Providence College, where he played Division I soccer.
Keith Kostrzewski