Totara Sales Director Case Study

Following multiple acquisitions and a strategic move from a channel-led to a direct sales model, Totara engaged Oakstone International to appoint a new Sales Director to lead this transition. Oakstone delivered a highly focused LMS/HCMS/EdTech search, introducing 8 shortlisted profiles, 100% of whom progressed to interview.

Despite market perception challenges and a constrained London-based talent pool, Oakstone secured a sector-proven, PE-backed SaaS sales leader with international experience and a strong track record in integrating acquisitions. The search was completed from briefing to signed contract in 13 weeks, delivering a leader aligned to Totara’s next phase of growth.

Totara Background

Sales Director Search Background

Sales Director Requirements

Oakstone’s Approach and Solution

Search Challenges

Search Results

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“The search market is very fragmented. There are the big guys who tend to operate at the top of the market, then the rest of it is a very fragmented market. Having a recruitment partner that's been around a long time and has got real tenure in its staff so they know the market, they know who's out there and type of capabilities you can tap into is essential. Getting a perspective on market rates and competition around certain roles is really helpful.

We've got an internal HR and recruitment team and they're certainly good at mid to junior roles, but when it comes to more specialist or senior roles, we want to work with people who have have got a reputation in the market and who are going to attract the right type of candidates as an extension of our own business, and give us access to a really solid talent pool. That’s certainly what Oakstone did for us.

Recruiting Senior go-to-market and commercial roles is pivotal to our value creation plan as an organisation. In my role in the go to market world it’s really important that I don't make missteps in recruitment. Working with the Oakstone team allows me to have certainty around the type and quality of candidate that’s put forward. It reduces a lot of the headache at the front end and gets me a solid shortlist quickly. They allow me to get into the detail of conversations with prospective candidates and not have to troll the market and sift through a lot of individuals. This allows us to move quickly when we get good quality candidates.

Good quality candidates want certainty as quickly as they can. Working with Oakstone allowed us to do that.”

- Iain Regan, CCO Totara

Totara 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.

Sales Director 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.

Sales Director 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.

Oakstone's 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.

Search 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.

Search 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.

Total time from briefing to contract signing: 13 weeks.

• Why use an executive search partner to find a Sales Director roles?

  Executive search firms provide access to senior, passive candidates with proven leadership and sector expertise. For Sales Director roles involving transformation or acquisition integration, search ensures higher quality shortlists and reduced hiring risk.

• How does Oakstone approach Sales Director searches differently?

  Oakstone International focuses on sector-specific networks, deep market knowledge, and long-term relationships. This enables the team to deliver high-quality shortlists quickly, even in fragmented or perception-challenged markets.

• What does a Sales Director role involve in a SaaS business?

  A Sales Director in a SaaS organisation is responsible for leading revenue execution, managing sales teams, and implementing go-to-market strategy. In scaling businesses, the role often includes transforming sales models, integrating acquisitions, and improving performance across regions.