# Heather Hennessy

> Heather Hennessy is a Waterloo, Ontario technology marketing executive and Encircle's Chief Marketing Officer. Her public career traces a distinctly local arc: a Conestoga College marketing student recognized for co-op work at Desire2Learn, a demand-generation leader at cybersecurity company eSentire, a marketing executive at Bonfire through its combination with GTY Technology, and now an executive translating the practical work of property restoration into a measurable software growth story.

- **Role:** Chief Marketing Officer at Encircle
- **Organizations:** Encircle, Bonfire Interactive, GTY Technology, eSentire, D2L (formerly Desire2Learn)
- **Education:** Business Administration - Marketing, Conestoga College
- **Known for:** Named a 2007 Conestoga College Co-op Student of the Year., Progressed through five increasingly senior marketing roles at D2L between 2008 and 2015., Advanced from marketing manager to senior director at eSentire between 2015 and 2018.

## Career timeline

- **2006-2008** — Worked at Desire2Learn first as a marketing assistant and then as a part-time marketing consultant; named a Conestoga College Co-op Student of the Year in 2007.
- **2008-2015** — Progressed through marketing specialist, field marketing, EMEA marketing and strategic marketing programs roles at D2L.
- **2012** — Appeared with the Desire2Learn team when Junior Achievement of Waterloo Region named the company Business of the Year.
- **2015-2018** — Advanced at eSentire from segment marketing manager to senior director of demand generation and performance analytics.
- **2018** — Became Bonfire Interactive's Vice President of Marketing and served as its marketing contact when the company announced its planned combination with GTY Technology.
- **2022** — Listed as GTY Technology's Vice President of Marketing in a public cooperative purchasing proposal.
- **2024** — Joined Encircle as Vice President of Marketing.
- **2026** — Serves as Chief Marketing Officer at Encircle.

## Achievements

- Named a 2007 Conestoga College Co-op Student of the Year.
- Progressed through five increasingly senior marketing roles at D2L between 2008 and 2015.
- Advanced from marketing manager to senior director at eSentire between 2015 and 2018.
- Built a senior marketing career across Waterloo-region software companies serving education, cybersecurity, public procurement and property restoration markets.
- Held the Vice President of Marketing role at GTY Technology.
- Advanced from Encircle Vice President of Marketing to Chief Marketing Officer.

## Latest updates

- **2026-08** — Listed as Chief Marketing Officer at Encircle.
- **2025-11** — Named as Encircle's press contact for the acquisition of The Edge, a rough-order-of-magnitude estimating tool for restoration contractors.
- **2025-09** — Named as Encircle's media contact for the launch of integrated field payments.
- **2025-06** — Publicly recruited a senior marketing programs manager and described marketing at Encircle as a visible growth driver.
- **2024-09** — Joined Encircle as Vice President of Marketing.

## Links

- Website: https://www.getencircle.com
- LinkedIn: https://www.linkedin.com/in/heather-b-hennessy

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Profile page: https://yespress.io/heather-hennessy
Published by YesPress — https://yespress.io
Last updated: 2026-08-25