Andrea Kassees — CEO
From day one of my 15+ year professional career, I’ve shown up with intention — to lead with truth, push boundaries, and grow in every direction. Success has never been about checking boxes or chasing vanity metrics. It’s about challenging status quo, delivering real, measurable results and creating space for others to rise alongside me. I’m known for being a straight shooter and leading by example— what I say is what I mean, and what I promise is what I deliver. But more than that, I show up as myself. I bring levity, make people feel seen, and create an environment where they can drop the mask, shoot straight with me, and work side-by-side to figure things out — with truth, always. That grounded authenticity earns trust quickly, builds deep partnerships, and inspires high-performing teams to show up fully. At Paycor, I was handpicked by the Chief Revenue Officer to be the national training resource for new hires — a reflection of my ability to lead, teach, mentor, and scale success across the org. I helped reps nationwide build out partner channels and self-generation strategies, while also exceeding a 4x sales quota myself — because I believe leading by example is the most powerful way to inspire performance. Today, I serve as the Head of Sales and Strategic Partnerships at Strive with a transformational approach. I build and execute go-to-market strategy, refine our value proposition and marketing engine, and develop strategic partnerships that fuel scalable revenue growth. My focus extends beyond revenue — creating human-first, high-performing environments where teams, clients, and partners thrive together. 📧 AK_Kassees@outlook.com 📞 414-380-3886
Stackforce AI infers this person is a Sales Leader in SaaS and HR Technology sectors.
Location: Milwaukee, Wisconsin, United States
Experience: 14 yrs 8 mos
Skills
- Sales Leadership
- Strategic Partnerships
- Sales Planning
- Business Development Strategy
- Sales Strategy
- Business Development
Career Highlights
- Exceeding sales quotas consistently by 4x.
- Mentoring new hires to drive team success.
- Building strategic partnerships for scalable growth.
Work Experience
Strive
Head of Sales and Strategic Partnerships (1 yr 2 mos)
Strategic Partnerships & Sales (7 mos)
Bringing Nature Home LLC
Co-Owner (1 yr 4 mos)
Dayforce
Sales Executive, Major Enterprise Accounts, Wisconsin (5 mos)
Paycor
Principal Sales Executive, Enterprise & Channel (2 yrs 6 mos)
Major Market Sales Executive, Milwaukee & Channel (1 yr 4 mos)
Direct Supply
Senior Business Development Manager, New Markets (3 yrs 9 mos)
Business Development Manager, New Markets (1 yr)
Account Manager Intern (6 mos)
Potbelly Sandwich Works
Manager (3 yrs 6 mos)
Certified Trainer (3 mos)
Associate Team Member (3 mos)
Education
Bachelor of Science in Business Administration and Marketing at Concordia University-Wisconsin