K
Power100 Contributor

Kira
Chesak

Director of Customer Success, ContractorFlow App

I live for those 'ah-ha' moments — building something that genuinely clicks for clients.
LinkedIn Profile
2022Years in Industry
NationalMarkets Served
MRCA 2025, NARI Milwaukee 2026Industry Events Represented
★ CONTRIBUTORPower100 Verified
About

Why Kira Chesak
Stands Out

Kira Chesak serves as Director of Customer Success at ContractorFlow App, a role she has held since June 2022, where she leads client relationships and champions the intersection of technology and operational excellence for home improvement contractors. With a background spanning Salesforce consulting at Canpango, SaaS delivery management at Ministry Brands and LPi, and executive operations at Silver Bullet Water Treatment Company, Kira brings a uniquely cross-functional perspective to customer success. She is recognized within the ContractorFlow team for aligning automation, analytics, and field leadership into seamless client outcomes. Kira has represented ContractorFlow at industry events including the MRCA 2025 conference and the NARI Milwaukee Spring Show, building relationships with remodelers across platforms. Her work has been highlighted in the context of Lindus Construction's culture of transparency and dependability, where her focus on technology integration and people-first leadership has made a measurable impact on contractor success.
Key Credentials
  • Director of Customer Success, ContractorFlow App (Jun 2022–Present)
  • SaaS Delivery Manager, Ministry Brands – WeGather product (2021–2022)
  • Senior Salesforce Consultant, Canpango – Greater Milwaukee Area (2017–2020)
  • Vice President of Administration, Silver Bullet Water Treatment Company (2013–2016)
  • B.S. International Management & French, University of Wisconsin–La Crosse
  • Paralegal Studies, Arapahoe Community College
Expertise Ratings

Domain
Mastery
Scores

Power100's evaluation of Kira Chesak's depth of expertise across the disciplines that define elite leadership in home improvement. Scored 1–10 based on verified performance, track record, and peer recognition.

Customer Success Leadership 9.5/10
SaaS Delivery & Implementation 9.3/10
Salesforce & CRM Expertise 9.2/10
Contractor Technology Enablement 9.4/10
Operational Strategy 9.1/10
Industry Relationship Building 9/10
Episode Appearances

Watch &
Listen

Executive Interviews

Executive Interview with Jennifer Rems, Lindsay Van Keuren, and Kira Chesak
Connected Network

Connected Contributors

Co-appearances on Power100 shows and articles.

Guest
JR
Jennifer Rems
ContractorFlow
 Guest
LV
Lindsay Van Keuren
ContractorFlow
Industry Recognition

Achievements &
Milestones

🏗️

Featured contributor on Lindus Construction Power100 profile

🎙️

Industry spokesperson at MRCA 2025 representing ContractorFlow

🤝

Represented ContractorFlow at NARI Milwaukee Spring Show 2026

📣

Named in Power100 Top 100 CEOs coverage alongside Andy Lindus

✍️

Published LinkedIn thought leadership on contractor tech and operations

🚀

Recognized internally as a leadership cornerstone of ContractorFlow's growth

Power100 Contributions
Customer Success Strategy SaaS Platform Delivery Salesforce CRM Implementation Contractor Technology Adoption Automation and Analytics Integration Operational Excellence in Home Improvement
What Kira Chesak Brings to the Table

Kira Chesak brings specialized knowledge across these domains, backed by real-world results and industry recognition.

The Organization
ContractorFlow
ContractorFlow App is a software platform purpose-built for home improvement contractors, offering tools that align technology, operations, and customer success to drive dependable business outcomes. Based in Baldwin, WI, ContractorFlow serves remodelers and contractors across the industry with a focus on automation, analytics, and field-to-office integration. The company actively engages the contractor community through industry events and thought leadership, positioning itself as a trusted technology partner for growth-minded home improvement businesses.
Power100 Contributors

Watch their work.

Kira Chesak shares their voice across the Power100 show network. Browse all of their episode appearances, or explore other contributors shaping the home improvement conversation.

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