Instructure Case Study

Instructure partnered with Oakstone International to replace its SVP EMEA and lead the next phase of European growth. Leveraging deep education technology and public sector sales expertise, Oakstone delivered 8 qualified candidates, progressed 5 to interview, and completed the hire within six weeks, securing a leader experienced in long sales cycles, enterprise education sales, and scaling regional teams.

Company Background

Search Background

The Challenge

Result

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Company Background

Instructure, Inc. is an educational technology company based in Salt Lake City, Utah, United States. It is the developer and publisher of Canvas, a web-based learning management system, and MasteryConnect, an assessment management system. The company is owned by private-equity firm Thoma Bravo.

• Founded in 2008 by Brian Whitmer and Devlin Daley.

• HQ Salt Lake City, USA. Approx 1500 employees.

• Total funding $89.1M (Series E)

• Learning technology company and the creator of the Canvas learning management system for K-12 and higher education (SaaS)

Search Background

• EVP people, Jeff Weber was recommended to reach out to Dan Hammond-Smith, Divisional Director at Oakstone to discuss European sales team expansion.

• Looking to replace the existing SVP EMEA as they we’re moving on.

• Looking for someone with experience of managing a sales teams in the education technology sector and who is a proven leader, used to longer sales cycles and public sector functionalities.

• Exclusive Contingent agreement

The Challenge

• Time: managing time expectations with the candidates as the internal hiring process had many touch points.

• The education sector is very small and therefore Oakstone had to make sure paths had crossed in the right way and references were collected.

Result

• The successful candidate had a background in the education space, consulting, and enterprise.

• They understood how to build teams from a cultural and numbers standpoint.

• Oakstone put forward 8 candidates, and Instructure interviewed 5 of these, which resulted in a successful hire.

• Total hiring time from search to signing: 6 weeks.

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• Why is hiring senior leadership in the education technology sector so challenging?

  The EdTech talent pool is relatively small, particularly at senior enterprise level. Leaders must combine deep education sector knowledge with experience navigating public sector procurement, long sales cycles, and complex stakeholder environments.

• Why are long sales cycles common in education and public sector SaaS?

  Education and government buyers often require budget approvals, compliance reviews, and multi-stakeholder decision-making. This creates longer, more consultative sales processes compared to commercial SaaS markets.

• How can Oakstone support EdTech companies hiring senior GTM leaders?

  Oakstone International specialises in executive search for SaaS and EdTech organisations, supporting the appointment of senior regional leaders across enterprise sales, public sector GTM, and global expansion.

I’m Hiring

Oakstone International are a specialised SaaS executive search and recruitment firm assisting companies globally. If you are looking for executive search assistance or would like to speak to a Divisional Director about future hiring assistance in EMEA, the US or APAC, contact Oakstone.

I’m Job Seeking

As a SaaS client-driven firm, we work exclusively for clients to find people with a specific set of skills and experience.

However, if you would like to submit your CV, it will be passed on to our divisional directors, and we will consider you for future roles that are appropriate to your background and goals.