Enterprise Account Executive, Community Foundations in Winnipeg

About Kindsight: Kindsight builds technology that helps fundraisers make a difference. For decades, Kindsight has supported the education, healthcare, and nonprofit sectors with fundraising tools and the largest charitable giving database on the market. As the leader in fundraising intelligence, Kindsight leverages real-time data and AI to help thousands of organizations around the world identify, manage, and engage with donors - at any scale.

Position Summary: The Enterprise Account Executive, Community Foundations owns new logo acquisition across the community foundation market in the United States and Canada. This is a build role. Community foundations are a new vertical for Kindsight, and the solution serving them is new to market. You will sell into a segment where Kindsight has limited brand presence, a short reference list, and no established playbook. The territory is greenfield, the pipeline is yours to create, and the messaging that works will be discovered in market and written down as you go.

The person in this seat needs strong commercial instincts in the absence of complete information, the discipline to prospect every week regardless of what else is happening in the funnel, the judgment to qualify hard and disqualify early and the credibility to earn executive conversations cold. You will be expected to convert what you learn from the market into repeatable narratives, proof points, and a playbook the broader team can run.

You will also need to understand how community foundations actually operate - donor-advised funds, fund accounting, grants management, constituent and fundholder engagement, board and committee dynamics, data trust, and reporting obligations to donors, nonprofits, professional advisors and the community. The role requires close partnership with Solutions Engineering, RFP, Marketing, Product, Professional Services, Customer Success and Revenue Operations, and a willingness to give Product direct, unfiltered market feedback while the offering matures.

What you’ll do:

• Drive New Logo Revenue: Own and exceed your new bookings target (subscription ARR and direct implementation revenue) by identifying, qualifying and closing net-new accounts.
• Relentless Outbound Prospecting: Build the vast majority of your own pipeline. You’ll research target foundations, execute multi-channel sequences, map key stakeholders and secure cold executive conversations every single week.
• Lead Complex Enterprise Deals: Run structured, multi-stakeholder sales cycles from initial discovery and custom value modeling through RFPs, procurement, board approvals and closing.
• Disqualify Hard & Build the Playbook: Protect your capacity by ruthlessly qualifying pipeline early. Capture market feedback, objection handling and win/loss insights to refine our GTM playbook and feed direct intel back to Product and Marketing.
• Cross-Functional Execution: Partner closely with Solutions Engineering, Professional Services, Customer Success and Revenue Operations to set clear project scopes, deliver initial customer value and secure our first reference accounts in the segment.

What We’re Looking For:

• 5+ years of Enterprise SaaS Sales: Proven track record of closing six-figure, complex deals involving multiple stakeholders, RFPs and formal procurement cycles.
• Proven Hunter Record: Demonstrated history of building a territory from a standing start, driving greenfield growth and self-sourcing the majority of your pipeline.
• Comfort with Early-Stage Ambiguity: Ability to operate with high commercial discipline in the absence of complete information, collateral or extensive reference customers.
• Exceptional Discovery & Closing: Strong business-acumen, executive presence and qualification habits (MEDDPICC background preferred).
• Travel: Willingness to travel as needed for key client meetings, sector conferences and association events.

Nice to Have:

• Deep domain knowledge of community foundations, donor-advised funds (DAFs), fund accounting or grantmaking workflows.
• Existing network or credibility within community foundation associations or professional advisor channels.
• Experience with Salesforce-native applications or complex data migrations.

Compensation Range: $260,000-350,000 CAD/$250,000-300,000 USD OTE annually, based on experience, market benchmarks and role complexity.

This advertised position is for an existing vacancy at Kindsight. At Kindsight, we’re proud to be a place where everyone belongs and has an equal opportunity to contribute, thrive and grow. We hire based on skills, potential, and impact, and we believe our differences fuel innovation. We welcome all individuals and do not discriminate on the basis of gender identity and expression, race, ethnicity, disability, sexual orientation, colour, religion, creed, gender, national origin, age, marital status, pregnancy, sex, citizenship, education, languages spoken or veteran status.

We leverage artificial intelligence (AI) tools to support certain aspects of our recruitment process. These tools may help with resume screening, drafting job descriptions, creating interview questions and occasionally identifying potential candidates. All hiring decisions are made by our people, not AI.