Totara Sales Director

Company Background

Search Background

Requirements

Our Approach and Solution

Challenges

Results

---

Company Background

Totara Learning Solutions is an open source learning technology to manage, develop and connect people. Their mission is to change how learning technologies are developed, delivered and purchased.

Totara needed a new Chief Commercial Officer (CCO) as part of its growth strategy. They reached out to Oakstone based on a recommendation from their executive chair and interim CEO, following a suboptimal experience with another firm in a previous executive search.

Search Background

Oakstone had previously placed Totara’s Chief Commercial Officer. Following several acquisitions and a strategic shift away from a channel-based model to a more direct sales approach, Totara needed a new sales leader to support this transformation. The role required someone adaptable, capable of integrating acquired businesses, and able to lead the transition to a more direct-centric go-to-market strategy.

Requirements

The ideal candidate needed to:

• Come from the LMS/HCMS/EdTech space, providing strong industry knowledge.

• Be an experienced, hands-on leader with exposure to both channel and direct sales models.

• Have international sales leadership experience.

• Commit to a hybrid working model with two to three days per week in the London office.

• Adaptable and flexible to work with new acquisitions.

Our Approach and Solution

We targeted a focused network within the LMS/HCMS/EdTech segment, prioritising candidates with relevant product knowledge and proven adaptability in integrating acquisitions.

We emphasised the long-term growth opportunity within Totara and reframed perceptions around its private equity ownership to attract interest.

Challenges

• Market perception: Some candidates viewed Totara as a slow-growth company without understanding the recent PE investment and growth plans.

• Location requirements: The need for regular London office presence narrowed the candidate pool.

Results

Oakstone introduced 8 profiles, all of which were interviewed. The final round of interviews included 3 of the original candidates.

The successful hire brought extensive sector knowledge, passion for the industry, and a strong track record in PE-backed, high-growth SaaS LMS businesses. His energy and expertise aligned perfectly with Totara’s strategy to scale aggressively through both acquisition and organic growth.