Sentry Insurance Foundation Inc

Quick Stats

• Annual Giving: $3,840,728 (2022)
• Success Rate: Not publicly disclosed
• Decision Time: Rolling basis - no fixed timelines
• Grant Range: $5,000 - $2,000,000 (most grants below $25,000)
• Geographic Focus: Wisconsin (especially Portage County/Stevens Point), Maui (Hawaii), and communities with Sentry field offices
• Total Grants Awarded: 78 grants (2022)
• Annual Scholarships: $600,000 to 237 students at 30 colleges/universities

Contact Details

Kalynn Pempek, Executive Director

• Email: kalynn.pempek@sentry.com
• Phone: 715-346-7636

Foundation Address: Sentry Insurance Foundation 1800 North Point Drive Stevens Point, WI 54481

Mailing Address: P.O. Box 8032 Stevens Point, WI 54481

General Phone: 715-346-6000 / 800-473-6879

Website: https://www.sentry.com/about-us/community-engagement

Alternative Contact for General Questions: Todd Swiontek: todd.swiontek@sentry.com / 715-346-6201

Overview

The Sentry Insurance Foundation Inc was established in 1964 (originally as the CN Jacobs Foundation) as the philanthropic arm of Sentry Insurance, a Fortune 650 mutual insurance company headquartered in Stevens Point, Wisconsin. As a tax-exempt 501(c)(3) independent private foundation, it supports approximately 85 organizations annually. The foundation contributed $3,840,728 in grants during 2022 across 78 awards, with grants ranging from $5,000 to $2 million, though most remain below $25,000.

The foundation's mission is "to improve the quality of life and build equitable communities where we live and work," with particular focus on Stevens Point (Sentry's 110-year headquarters location), the island of Maui (home of The Sentry PGA TOUR event), and communities where Sentry maintains field offices. The foundation emphasizes strategic giving in education, workforce development, United Way support, and local nonprofits building stronger communities. In 2020, Sentry won the Deloitte Wisconsin 75™ Distinguished Performer Community award for its focus on giving back to the community.

Funding Priorities

Grant Programs

Major Institutional Grants (transformational gifts, typically $1M+)

• Recent examples: $10 million to UW-Stevens Point School of Business and Economics (2022, largest gift in foundation history); $2 million to Medical College of Wisconsin-Central Wisconsin Campus (2019)

Technology & Education Innovation Grants ($100,000 - $2M)

• Multi-year technology initiatives for K-12 schools
• Since 2009: $17 million total to Stevens Point area schools for technology enhancement
• Recent: $1.7 million for 2023-2025 Stevens Point Schools Technology Innovation Initiative

Community Impact Grants ($5,000 - $100,000, rolling basis)

• Most typical grant range: under $25,000
• Supports local nonprofits, arts organizations, youth development, health services
• No fixed deadlines; applications accepted year-round

Scholarship Programs ($600,000 annually)

• 237 scholarships per year across 30 colleges and universities
• Sentry Scholars Program (Maui): 12 renewable scholarships annually to public high school students attending University of Hawai'i system ($1,500-$2,500 each)
• UW-Superior Leadership Scholarships: Two $2,500 renewable scholarships
• El Paso Scholarships: Four scholarships ($1,000-$2,500)
• 13+ annual empowerment scholarships for underserved communities

Matching Gift Program (for Sentry employees and retirees only)

• 1:1 match from $25 to $7,500 per person per year
• Supports individual employee charitable giving

Priority Areas

Education (top priority)

• K-12 technology and STEM programs
• Higher education institutional support
• Data analytics and business education programs
• Scholarship opportunities for students
• Educational equity initiatives for underrepresented students

Workforce Development

• Career readiness programs
• Talent pipeline development
• Insurance education programs
• Entrepreneurship centers
• Programs creating jobs and economic opportunities

United Way Support

• Major annual focus (2025 campaign raised $1.85 million company-wide)
• Foundation provides matching funds for employee contributions
• Focus on communities where Sentry operates

Community Quality of Life

• Youth development and at-risk youth programs (e.g., $1.5M to Rawhide Youth Services)
• Arts and culture (Central Wisconsin Symphony Orchestra, Portage County Cultural Fest)
• Health and human services
• Mental health support (e.g., $1M for Maui youth mental health after 2023 wildfires)
• Athletics and recreation (Special Olympics Wisconsin, First Tee programs)

Diversity, Inclusion & Equity

• $1 million dedicated to long-term diversity and inclusion efforts
• Supports 12+ nonprofits focused on diversity and inclusion
• Programs serving underserved and underrepresented communities
• Boys & Girls Club Youth for Unity initiatives
• Educational programs for historically underrepresented students

What They Don't Fund

• Individuals (except through established scholarship programs)
• Political organizations or lobbying groups
• Third-party fundraisers
• Organizations outside their geographic footprint (Wisconsin, Maui, Sentry field office communities)

Governance and Leadership

Kalynn Pempek - Executive Director

• Email: kalynn.pempek@sentry.com
• Phone: 715-346-7636

Pete McPartland - Chairman and CEO, Sentry Insurance (parent company)

While specific foundation trustees are not publicly listed in accessible databases, the foundation operates as an independent 501(c)(3) private foundation affiliated with Sentry Insurance Group.

Leadership Perspectives

Pete McPartland, Sentry's Chairman and CEO, emphasizes the connection between community investment and business success:

On employee engagement: "Our employees are caring and community-minded, demonstrating unmatched generosity year after year. Their strong participation reflects a culture of engagement that sets Sentry apart."

On community partnerships: "At Sentry, we firmly believe the presence of a strong university is critical, not only for our company but for the community. As a Fortune 650 company, headquartered in a small midwestern city, we're able to thrive due in large part to UW-Stevens Point. The university is creating career-ready graduates and contributing to a community culture that allows us to recruit and retain well educated, talented employees."

On commitment to Maui: "Helping the Maui community recover and heal is deeply personal for us. Our commitment to Maui extends beyond our role as the title sponsor of The Sentry... We've embraced Maui as our home, just as we've called Stevens Point home for 110 years."

Application Process & Timeline

How to Apply

The Sentry Insurance Foundation accepts unsolicited grant requests from nonprofits through a simple letter of inquiry process:

Method: Send a letter by mail or email describing:

• The nature of your organization
• Your organization's work and mission
• The specific amount of contribution requested
• How your work aligns with foundation priorities

Submission Address: Sentry Insurance Foundation P.O. Box 8032 Stevens Point, WI 54481

Email: kalynn.pempek@sentry.com

No formal application form required - the foundation uses a streamlined letter-based approach to reduce administrative burden on applicants.

Decision Timeline

• Rolling basis: Sentry does not typically implement submission deadlines or restrictions on awards
• Applications accepted year-round
• Decision timeframe: Not publicly disclosed; varies by grant size and complexity
• Large institutional grants likely require more extensive review and board approval
• Smaller community grants may have faster turnaround

Success Rates

Success rate data is not publicly disclosed. The foundation made 78 grants totaling $3,840,728 in 2022, supporting approximately 85 organizations annually. This suggests selective grantmaking focused on strategic community partnerships rather than broad distribution.

Reapplication Policy

Not explicitly stated. Given the foundation's rolling application process and ongoing relationships with many grantees (e.g., multi-year technology initiatives with Stevens Point schools), repeated applications appear to be acceptable. Organizations are encouraged to maintain communication with foundation staff.

Application Success Factors

Geographic Alignment is Critical

The foundation's giving is highly focused on specific communities:

• Portage County/Stevens Point, Wisconsin (headquarters location, 110+ years) - receives significant majority of funding
• Maui, Hawaii - special focus due to Sentry's PGA TOUR event (The Sentry) and company commitment
• Communities with Sentry field offices - secondary priority

Organizations outside these areas are unlikely to receive funding unless they have direct connection to Sentry's strategic interests.

Strategic Fit with Core Priorities

The foundation shows clear preference for:

• Education initiatives with measurable workforce development impact (e.g., $4M UWSP data analytics program, $17M K-12 technology initiative)
• Programs addressing equity gaps in education and opportunity for underserved communities
• Multi-year partnerships rather than one-time grants for sustainable impact
• Technology and innovation in education (documented pattern of significant tech investments)

Demonstrate Community Impact and Sustainability

Successful grantees show:

• Clear connection to improving quality of life in Sentry communities
• Programs that build stronger, more equitable communities (foundation mission language)
• Capacity for long-term partnership and relationship building
• Outcomes that benefit workforce development and economic opportunity

Examples of Funded Projects

Understanding what the foundation has funded provides insight into priorities:

Large-Scale Educational Investments:

• $10 million to UW-Stevens Point for Sentry School of Business and Economics (2022) - created entrepreneurship center, Center for Women's Equity, Development and Leadership
• $2 million to Medical College of Wisconsin-Central Wisconsin Campus for Sentry Deanship (2019) - addressing physician shortage in northern Wisconsin
• $1.7 million for Stevens Point Schools Technology Innovation Initiative (2023-2025)

Community Organizations:

• University of Wisconsin Oshkosh Insurance Program
• Stevens Point Area Catholic Schools
• Central Wisconsin Symphony Orchestra
• Special Olympics Wisconsin
• Portage County Cultural Fest
• Rawhide Youth Services ($1.5M for at-risk youth transformation)
• Maui Food Bank ($250,000 COVID-19 relief)
• First Tee (youth development in underserved communities)

Foundation Culture Emphasizes Relationships

Based on CEO quotes and giving patterns, the foundation values:

• Long-term community partnerships - note 110-year Stevens Point commitment, growing Maui relationship
• Employee engagement - strong internal culture of giving and volunteerism
• Strategic alignment - grants support broader company success through workforce development
• Equity and inclusion - $1M dedicated commitment, consistent language about building "equitable communities"

Application Best Practices

While not explicitly stated by the foundation, successful approaches likely include:

1. Clearly articulate geographic connection - explain presence in Stevens Point, Maui, or Sentry office community
2. Align language with foundation priorities - use terms like "quality of life," "equitable communities," "workforce development"
3. Show sustainability beyond grant - multi-year impact, partnerships, matching funds
4. Quantify impact where possible - student numbers, workforce outcomes, community reach
5. Consider relationship building - the foundation supports ~85 organizations annually out of presumably many more inquiries, suggesting relationship-based giving

Key Takeaways for Grant Writers

• Geography matters immensely: Focus on Stevens Point/Portage County, Maui, or Sentry field office locations. Outside these areas, chances are minimal.

• Education and workforce development are top priorities: The foundation has demonstrated willingness to make transformational gifts ($2M-$10M) for education initiatives with clear workforce development outcomes.

• Think multi-year partnerships, not one-time grants: The foundation's largest successes are sustained initiatives (e.g., $17M over 15+ years for K-12 technology).

• Application process is refreshingly simple: Just send a letter - no complex forms or lengthy proposals required for initial inquiry.

• Rolling basis means no deadline pressure: Applications accepted year-round; plan outreach when your organization is ready.

• Equity and inclusion alignment strengthens applications: The foundation has dedicated $1M specifically to diversity and inclusion efforts and consistently emphasizes "equitable communities."

• Show connection to Sentry's business interests: The foundation supports programs that create talent pipelines and strengthen communities where Sentry employees live and work - make this connection explicit if applicable.

References

1. Sentry Insurance Foundation - Community Engagement. Sentry Insurance. https://www.sentry.com/about-us/community-engagement (Accessed February 12, 2026)

2. Education and Workforce Development Programs. Sentry Insurance Foundation. https://www.sentry.com/about-us/community-engagement/education-workforce-development (Accessed February 12, 2026)

3. Diversity and Inclusion Initiatives. Sentry Insurance Foundation. https://www.sentry.com/about-us/community-engagement/inclusion (Accessed February 12, 2026)

4. Sentry Insurance Foundation Inc. Inside Philanthropy. https://www.insidephilanthropy.com/find-a-grant-places/wisconsin-grants/sentry-insurance-foundation (Accessed February 12, 2026)

5. Sentry Insurance Foundation Inc - Form 990 Filings. ProPublica Nonprofit Explorer. https://projects.propublica.org/nonprofits/organizations/391037370 (Accessed February 12, 2026)

6. "Sentry donates $10M to UW–Stevens Point for business school." Sentry Insurance News. December 15, 2022. https://www.sentry.com/about-us/company-news-and-events/sentry-foundation-donates-10-million-for-university-of-wisconsin-stevens-point-business-school

7. "Sentry supports medical education with $2 million gift." Sentry Insurance News. December 2019. https://www.sentry.com/about-us/company-news-and-events/medical-education

8. "Sentry wins Deloitte Wisconsin 75™ community award." Sentry Insurance News. 2020. https://sentry.com/about-us/company-news-and-events/sentry-wins-deloitte-award

9. "Sentry raises $1.85M in 2025 United Way campaign." Sentry Insurance News. 2025. https://www.sentry.com/about-us/company-news-and-events/sentrys-2025-united-way-campaign-raises-1-85-million-to-support-communities-nationwide

10. "Sentry Provides 1.7M To Stevens Point Schools Through Technology Innovation Initiative." Sentry Insurance News. https://www.sentry.com/about-us/company-news-and-events/sentry-provides-17m-to-stevens-point-schools-through-technology-innovation-initiative

11. "Sentry Foundation awards scholarships to 12 Maui students." Sentry Insurance News. 2024. https://www.sentry.com/about-us/company-news-and-events/sentry-foundation-awards-scholarships-to-12-maui-students

12. Sentry Insurance Foundation Inc. Foundation Directory. Candid. https://fconline.foundationcenter.org/fdo-grantmaker-profile?key=SENT001 (Accessed February 12, 2026)

13. Sentry Insurance Foundation Inc. 990 Report. Instrumentl. https://www.instrumentl.com/990-report/sentry-insurance-foundation-inc (Accessed February 12, 2026)