Chris Kiefer

Speaking

AI for contractors, from someone who wired the systems himself

Chris Kiefer spent three years connecting the CRM, estimating, production and accounting of a $10M painting company so its numbers could be trusted. Today he runs paintOS, which does the same for 24 painting companies. His talks give contractors the model and the next step, without the hype and without a sales pitch.

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Chris Kiefer in a navy suit, arms crossed, leaning on a brick wall

$10M to $21M

Webfoot's growth while Chris ran marketing and built its systems

24

painting companies running on systems Chris designed

210+

episodes of The Pursuit of Purpose podcast

3 years

wiring CRM, estimating, production and accounting together by hand

"I couldn't trust a single number I was looking at."

Chris trained as an engineer, ran an agency, and then took the marketing director seat at Webfoot, a $10M painting company with a $1M a year marketing budget. It had a CRM, production software, accounting software and an in house video team. A few months in, he realized none of the numbers agreed, because none of the systems talked to each other.

So he spent three years building the connections himself: lead intake to sales, sales to estimating, estimating to production, production to job costing and the books. Webfoot went from $10M to $21M over that stretch. Marketing directors at other painting companies asked him to set up the same thing, and that work became paintOS.

That is the perspective he brings to a stage. He has sat in the owner's meeting where nobody can say which marketing brings in the profitable jobs, and he has built the plumbing that answers it.

Programs

Three ways to bring Chris in

Keynote · 45 to 60 minutes

You Already Have Software. That's the Problem.

Most contractors past a few million in revenue run on five or six good tools that never talk to each other. The CRM says one thing, production says another, and QuickBooks has the real numbers a month late. This talk shows why AI stalls in that setup, which connection to make first, and what a company looks like once one job typed once lands everywhere it needs to be.

They leave with

  • A six system map of their own company: marketing, sales, estimating, production, accounting and reporting
  • The one broken handoff costing them the most, and how to find it this week
  • Why automating a messy process makes it worse, and the order to fix things in
  • A plain definition of what AI can do with their data today

Best for: Association conferences, trade shows, peer groups and franchise meetings.

Workshop · 2 to 4 hours

Find Your AI Power Score

A working session built on the AI Power Score, the four part model Chris uses with painting companies. Each attendee scores their own company, sees where they sit against the room, and leaves with a written commitment their leadership team can act on the following Monday. Laptops and phones out, real company data, no theory lecture.

They leave with

  • Their own four numbers: Operator, Data, Factor and Leadership
  • A dot on the grid showing which lever moves them fastest
  • A 30 day plan to test widely, then commit to one workflow
  • A leadership commitment with a date, a headcount and a measure of success

Best for: Leadership teams, masterminds and the breakout track of a conference.

Recap or panel · 30 minutes

What Did You Just Hear

Conferences hand people a lot of AI in a single day. Chris closes the day by sorting it: what matters for a contracting business, what to ignore, and the next step to take. He also moderates contractor panels, drawing out the specifics owners want to hear from their peers.

They leave with

  • The day's sessions boiled down to what applies to their company
  • A self assessment that ranks them against the room
  • One move for Monday that costs nothing to start

Best for: The end of a conference day, a panel slot, or a virtual member event.

The ideas

What runs through every talk

The AI Power Score

AI Power = L · (D + Op)^Fa. Leadership, Data, Operator and Factor. Every variable is something the owner controls, and none of them is which tool you bought. Because Data and Operator add, a beginner with clean, connected data gets as far as an expert with a mess.

Connect before you automate

Automation on top of a broken handoff makes the mess run faster. Chris starts every room with the six systems every contractor already has and shows where information gets typed twice, because that is where money leaks and where AI has nothing reliable to read.

Leaders invest, teams experiment

Adoption moves when the leadership team writes it down: by this date, this many people will use AI to do this work. Then people get permission to test widely for 30 days, and the company commits to the one workflow that proved itself.

The six systems every contractor runs

Marketing
Sales
Estimating
Production
Accounting
Reporting

Each one is usually a decent tool on its own. The trouble lives in the gaps between them, and that is where the keynote spends its time.

From contractors who work with Chris

“There is nobody in the painting industry who understands how to actually apply AI like Chris and Cody.”
Tom HeilerOwner and Founder, Heiler Painting
“Our first year with PaintOS we went from $2.1M to $2.9M and I finally have numbers I trust enough to make decisions on. Now I'm building my own AI reports on top of what they set up, which is not something I could have done two years ago.”
Matt MasonOwner, A&A Painting
“We have worked with Chris and his team for almost 4 years and one thing I have always admired is his ability to keep looking ahead at what is possible with automations and streamlining processes.”
Sean KennedyPresident, Kennedy Painting

Recent stages

CPIA Leadership Conference

Nashville, September 2026. Moderator of the contractor AI panel and the Day 1 AI recap.

The Pursuit of Purpose

Host of more than 210 long form conversations with founders and operators.

Book Chris

Check a date

Tell Chris about the event and the room. He replies personally, and every booking starts with a short call about your audience.

Planning logistics? Bios, the introduction script and room setup are on the meeting planner page.

Questions from event planners