Andrea Kassees

CEO

Milwaukee, Wisconsin, United States14 yrs 8 mos experience
Highly Stable

Key Highlights

  • Exceeding sales quotas consistently by 4x.
  • Mentoring new hires to drive team success.
  • Building strategic partnerships for scalable growth.
Stackforce AI infers this person is a Sales Leader in SaaS and HR Technology sectors.

Contact

Skills

Core Skills

Sales LeadershipStrategic PartnershipsSales PlanningBusiness Development StrategySales StrategyBusiness Development

Other Skills

Go-to-Market StrategyTeam DevelopmentStakeholder ManagementProduct StrategyGoal SettingRelationship BuildingSales CoachingPresentationsConsensus BuildingMicrosoft OfficeChannel SalesPresentation SkillsDemand GenerationStrategic ThinkingMicrosoft Excel

About

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

Experience

14 yrs 8 mos
Total Experience
3 yrs 3 mos
Average Tenure
1 yr 9 mos
Current Experience

Strive

2 roles

Head of Sales and Strategic Partnerships

Promoted

Mar 2025Present · 1 yr 2 mos · Remote

  • As Head of Sales and Strategic Partnerships at Strive, I serve as a revenue architect, building and executing go-to-market strategy, sharpening our value proposition and marketing engine, and developing strategic partnerships and business development initiatives that drive scalable revenue growth.
Sales PlanningStrategic PartnershipsBusiness Development StrategyGo-to-Market StrategySales Leadership

Strategic Partnerships & Sales

Aug 2024Mar 2025 · 7 mos · Remote

  • During my short time in this role before being transitioning into leadership, I focused on building pipeline and uncovering new business opportunities from the ground up. In just three months, I led more prospect and partner meetings than the company had seen in the previous year—accelerating our outreach and helping Strive break into new markets. I identified and established new relationships with brokers, benefit strategists, and distribution partners across regional and national landscapes, laying a strong foundation for long-term growth
Sales PlanningTeam DevelopmentStakeholder ManagementProduct StrategyGoal SettingBusiness Development Strategy+4

Bringing nature home llc

Co-Owner

Jan 2025Present · 1 yr 4 mos · Bay View, Wisconsin · Hybrid

  • At Bringing Nature Home, we are dedicated to restoring native landscapes in urban areas, creating vibrant, sustainable ecosystems that support pollinators, wildlife, and healthier communities. Our mission is to reconnect people with nature through thoughtful design, education, and hands-on restoration work that transforms ordinary yards into living habitats!
  • As Co-Owner, I am passionate about advancing this mission by fostering environmental stewardship, promoting biodiversity, and educating our community about the benefits of native plants. We believe that every green space has the potential to contribute to climate resilience, improve urban ecology, and inspire a deeper connection to the natural world.

Dayforce

Sales Executive, Major Enterprise Accounts, Wisconsin

Jan 2024Jun 2024 · 5 mos · Wisconsin, United States · Remote

  • During my time at Dayforce, I was responsible for developing a new territory in Wisconsin, targeting organizations with 1,000 to 3,500 employees. I established a pipeline of 15 high-potential accounts from a pool of 130 assigned accounts and I organized two high-impact events showcasing my ability to drive results in an untapped market in a short amount of time. My proactive approach to prospecting consistently surpassed my peers in activity metrics, leading to significant pipeline growth. Through independent marketing efforts and strategic engagement with top executive contacts, I generated $750,000 in pipeline for Q3 & Q4 FY24 and positioned the territory for future success with $2.5 million in pipeline for FY25.
  • Additionally, I implemented an independent mentorship program that enhanced the skills of my Business Development Representatives, leading to increased morale and an external promotion for one of my mentees.
  • Achievements:
  • Generated substantial pipeline growth: $750,000 in pipeline for FY24, and $2.5 million in pipeline for FY25.
  • Established a pipeline of 15 high-potential accounts out of 130 assigned, delivering immediate impact in a previously untapped region.
  • Successfully profiled two distinct 200-account territories within two months, adapting swiftly to reassignment and organizational changes.
  • Conceptualized, organized, and executed two high-impact events—MKE Dine & Dayforce, Dine & Dayforce @ Lambeau Field
  • Directed all facets of event planning and execution, including territory profiling, crafting targeted marketing strategies, developing custom gifting campaigns, and conducting multi-channel outreach.
  • Drove attendance from 50 key prospects and clients across all events, securing a critical RSVP for an active $350K Q3 FY24 opportunity.
  • Consistently outpaced peers in prospecting and activity metrics, developing a highly effective, tailored campaign that maximized engagement and attendance at key events.
Consensus BuildingMicrosoft OfficeChannel SalesPresentation SkillsDemand GenerationStrategic Thinking+74

Paycor

2 roles

Principal Sales Executive, Enterprise & Channel

Promoted

Jul 2021Jan 2024 · 2 yrs 6 mos · Remote

  • During my time at Paycor, I managed a $1,000,000 quota, four times larger than my peers, demonstrating my ability to drive results through direct prospecting and building a strong channel network. I covered Wisconsin, mid-market and enterprise accounts with over 500 employees.
  • I was selected by our CRO to mentor new hires nationwide, extending beyond my official role. My coaching emphasized self-generation techniques and establishing broker networks, allowing me to engage with an average of three new hires per week. This hands-on approach equipped them with essential skills for success and fueled my passion for leadership.
  • I played a significant role in Paycor’s growth during its transition to a publicly traded company through an IPO, deepening my understanding of corporate operations and strategic planning, which helped me cultivate lasting partnerships with brokerage firms, technology consultants, and financial advisors.
  • A notable achievement was establishing a partnership with The Retirement Advantage, a national TPA with over 9,000 clients. I built the relationship from the ground up and streamlined the referral process, resulting in 3-5 emailed introductions per week and securing their HRIS business. This partnership remains active and continues to generate leads for Paycor. https://tra401k.com/prime/
  • Achievements:
  • Million Dollar Club Member: 2021, 2022, 2023
  • FY23:
  • Platinum club qualifier FY23
  • Mid-year club qualifier FY23
  • Sold $1,464,950.61 Pre-Splits with down-market reps, $1,191,990.88 sold post splits on $1,000,000 Quota *Note: $1,191,990.88 is including a negative audit of ($317,688.49) in Paycor caused no-starts. Meaning my total revenue booked for the company was $1,509,679.37*
  • 119% to Plan, Finish in top 10% of all sales
  • FY22:
  • Platinum club qualifier FY22
  • Mid-year club qualifier FY22
  • Sold $960,542.95 on 1,000,000 Quota
  • 96% to Plan, Finish in top 10% of all sales
  • Platinum club qualifier FY22
  • Mid-year club qualifier FY22
Consensus BuildingMicrosoft OfficeChannel SalesPresentation SkillsDemand GenerationStrategic Thinking+86

Major Market Sales Executive, Milwaukee & Channel

Mar 2020Jul 2021 · 1 yr 4 mos · Remote

  • In this role, I specialized in HR technology consulting for organizations ranging from 50 to 500 employees, focusing on self-generation strategies and building a robust partner network. My consistency in self-generation was evident as I completed 25-50 mailers a week, created marketing cadences, and made my own marketing pieces. I excelled in building new business relationships, averaging 5 new partner meetings and 3 first-time appointments with potential clients a week.
  • My efforts were instrumental in launching and leading the team in Wisconsin, where I achieved the distinction of being the #1 ranked representative on the seller scorecard nationally. Notably, I was among the first five individuals to qualify for club in my inaugural year in this industry, highlighting my rapid impact and success.
  • Achievements:
  • Sold $720,542.25 on $250,000 Quota, 288% to Plan
  • Top Rookie of the Year based on % to plan & revenue
  • Mid-year club qualifier FY21
  • Platinum club qualifier FY21
  • #1 ranked Paycor rep nationally on the annual seller scorecard 2020 (first year in industry)
Consensus BuildingMicrosoft OfficeChannel SalesPresentation SkillsDemand GenerationStrategic Thinking+84

Direct supply

3 roles

Senior Business Development Manager, New Markets

Jun 2016Mar 2020 · 3 yrs 9 mos

  • Drove growth for Direct Supply, specializing in skilled nursing, senior living, and healthcare equipment & technology, by strategically expanding into diverse healthcare markets. Never missed quota and was BDM or the year twice out of four years eligible.
  • Built and managed relationships with Group Purchasing Organizations (GPOs) to drive business into mental health facilities, adult daycares, and independent hospitals. Demonstrated strong expertise in understanding healthcare needs, fostering partnerships, and tailoring solutions to meet the demands of various facilities, including mental health and specialized care environments. Notably, I found similarities in the Healthcare industry to the Hotel & Hospitality industry and produced impressive results driving revenue in this segment-which had never been done prior to my contributions.
  • In addition to business development, I served as a team mentor and the go-to resource for coaching and brainstorming strategies. This allowed me to share my expertise with colleagues, foster collaboration, and contribute to our team’s success.
  • Achievements:
  • Business Development Manager of the Year Award (2017, 2019), #1 Ranked BDM in company
  • Budget Buster Award (2015, 2016, 2017, 2018, 2019)
  • 4 Quarter Budget Buster Award (2016, 2019)
  • Quarterly Elite Performer Award (8x from June 2015-2019)
  • 2019: $2,561,967 sold on $1,412,889 Quota 288% to Plan, Revenue Growth 81.33%, Margin Growth 64.2%, Order Growth 21.39%,
  • 2018: $2,278,520 sold on 2,051,056 Quota 181% to Plan, Revenue Growth 11.09%, Margin Growth 6.86%, Order Growth 9.95%,
  • 2017: $1,741,193 sold on $929,094 Quota 187% to Plan, Revenue Growth 87.41%, Margin Growth 74.09%, Order Growth 4.71%,
  • 2016: $2,054,869 sold on $1,374,911 Quota 149% to Plan, Revenue Growth 49.45%, Margin Growth 47.12%, Order Growth 18.92%,
Microsoft OfficePresentation SkillsMicrosoft PowerPointDemand GenerationStrategic ThinkingMicrosoft Excel+62

Business Development Manager, New Markets

Jun 2015Jun 2016 · 1 yr

  • 2015: $1,248,758 sold on $697,284 Quota 179% to Plan, Revenue Growth 79.09%, Margin Growth 67.02%, Order Growth 18.21%,
  • Top Rookie Business Development, 2015

Account Manager Intern

Dec 2014Jun 2015 · 6 mos

  • I started my journey at Direct Supply as an Account Manager Intern, where I quickly transitioned to an Business Development role. During my time as an account manager, I honed my selling skills while managing a territory of healthcare organizations. My strong business development traits and drive for success quickly led to a promotion to a Business Development role, recognizing my potential for higher earnings and growth. The traits I exhibited—true hunter mentality, grit, and creativity to open doors and develop business where no one else could—were instrumental in this advancement.
  • My rapid advancement to this senior role highlights my ability to learn at an accelerated rate and my relentless commitment to excellence in everything I do.

Potbelly sandwich works

3 roles

Manager

Promoted

Jan 2012Jul 2015 · 3 yrs 6 mos · On-site

  • At Potbelly Sandwich Works, the core value of positive energy perfectly aligned with my biggest strength. I thrived in this environment and developed an outstanding relationship with my general manager, who taught me the importance of running a business with a focus on people before profits. As a manager, I dedicated myself to continuous development in business management.
  • In this role, I gained comprehensive experience in managing various aspects of the business, including personnel, customers, sales, and profits. I was responsible for product ordering, employee training, and development, money management, and direct customer service. My responsibilities allowed me to enhance my skills in leadership and effective business operations.
  • Under the mentorship of my general manager, I evolved into a better and more effective leader. My dedication and positive energy earned me two Associate of the Month honors. Additionally, I was promoted from associate to certified trainer to manager in under a year, showcasing my rapid growth and commitment to excellence in my role.
Microsoft OfficeMicrosoft PowerPointStrategic ThinkingMicrosoft ExcelLead GenerationMarketing Strategy+52

Certified Trainer

Oct 2011Jan 2012 · 3 mos · On-site

Associate Team Member

Jul 2011Oct 2011 · 3 mos · On-site

Education

Concordia University-Wisconsin

Bachelor of Science in Business Administration and Marketing

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