HiBob Upper Mid-Market Sales Manager Case Study

HiBob partnered with Oakstone International to support the search for a Mid-Market Sales Manager in the UK.

Working alongside the team at HiBob, Oakstone introduced 5 candidates, 3 of whom progressed to interviews. Through an in-depth search, Oakstone identified and engaged the right hire in just 8 weeks.

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About HiBob

Hibob, established with the vision to revolutionise HR technology, has successfully crafted an innovative and data-centric platform named Bob, designed to align with the evolving nature of contemporary work environments. Bob caters to the needs of a global, remote, and collaborative workforce, setting a new standard for Human Resources Information Systems (HRIS).

Since its inception in late 2015, bob has experienced remarkable growth, consistently achieving triple-digit year-over-year expansion. It has emerged as the HRIS of choice for over 1,000 forward-thinking companies, ranging from modern startups to midsize enterprises and multinational corporations. These organisations recognise the indispensable role of a robust and flexible HR tech suite as a driving force behind organisational success.

The platform's popularity is underscored by its adoption by renowned and fast-growing companies on a global scale, including industry leaders like Monzo, Happy Socks, Gong, Fiverr, and VaynerMedia. These dynamic enterprises place their trust in bob to facilitate HR and managerial functions, allowing them to seamlessly connect, engage, develop, and retain top talent.

Bob's impact extends beyond its feature-rich capabilities; it has become an integral part of the success stories of companies that understand the pivotal role of cutting-edge HR technology in navigating the complexities of the modern workplace. With its user-friendly interface, advanced analytics, and adaptability to various organisational structures, bob continues to be a driving force in shaping the future of HR tech, empowering businesses to thrive in the ever-evolving landscape of work.

• Company Location: HQ in Tel Aviv, Israel

• Founded: 2015

• Number of Employees: Now 2000+

• Stage: Series D

Search Background

Historically, HiBob’s sales leadership had evolved organically, with high-performing SMB salespeople stepping into management roles. However, as the company matured and began targeting larger customers and selling more complex deals, there was a clear need to introduce more experienced leadership.

HiBob had undertaken significant internal efforts to fill the role of an Upper Mid-market Sales Manager in the UK but found challenges when trying to identify candidates with the right balance of leadership capability, deal complexity experience, and cultural alignment. Recognising the benefits of a more structured search approach, the HiBob team partnered with Oakstone for a consultative and targeted search process.

Requirements

HiBob was looking to hire an Upper Mid-Market Sales Manager in the UK.

While classified as mid-market, the role carried enterprise-level complexity due to deal size and stakeholder alignment.

Key requirements included:

• Proven experience leading new business sales teams in high-growth SaaS environments

• Strong exposure to complex, multi-threaded deal cycles (ideally MEDDPICC or similar frameworks)

• Ability to operate in a fast-paced, scaling organisation

• A coaching-led leadership style, capable of developing increasingly senior sales talent

• Cultural alignment with a dynamic, collaborative, and evolving team environment

HR tech experience was considered advantageous but not essential.

Oakstone’s Approach and Solution

Oakstone leveraged its longstanding relationship with HiBob and deep network within SaaS GTM leadership to execute a highly targeted search.

Given the perception challenges around “mid-market” roles, the Oakstone team adopted a consultative and narrative-led outreach strategy. Rather than leading with job title or segment, Oakstone positioned:

• The scale and complexity of the opportunity

• The growth trajectory of HiBob

• The strategic impact of the role within the organisation

This approach enabled Oakstone to engage candidates who would typically self-select out of mid-market roles, particularly those with enterprise or large-deal experience.

Oakstone utilised its curated network of proven SaaS sales leaders, built through previous searches, and new contacts who were established through running new searches, to identify individuals with the precise blend of:

• Deal complexity experience

• Leadership maturity

• Appetite for scale-up environments

The search remained confidential, allowing Oakstone to control the narrative against preconceived perceptions of the company or role.

Search Challenges

1. Market Perception vs Reality
HiBob was still widely perceived as an SMB-focused, transactional sales environment, despite evolving into a high value platform sale with complex deals. This created friction in attracting senior talent aligned to enterprise-level selling.

2. Role Positioning
The “mid-market” label risked deterring candidates with the required experience, even though the role itself demanded enterprise-level capability.

3. Title Misalignment
HiBob’s use of traditional “manager” titles (true people leadership roles) conflicted with broader SaaS market norms, where similar titles often refer to individual contributors. This created perceived step-back concerns for candidates.

4. Candidate Calibration
HiBob’s hiring bar was exceptionally high. Candidates needed to balance:

• Strategic leadership experience

• Hands-on deal exposure

• Cultural alignment with a fast-scaling organisation  

Search Results

Oakstone delivered a highly focused shortlist:

• 5 candidates introduced

• 3 candidates progressed to interview

• 1 candidate successfully hired

The successful hire demonstrated:

• Strong experience across HR and adjacent SaaS domains

• A track record of leading teams selling complex, high-value deals

• Deep understanding of MEDDPICC and structured sales processes

• Proven ability to operate in scale-up environments

• A coaching-first leadership style aligned with HiBob’s development needs

The successful candidate progressed through the full process and was ultimately selected as the standout individual, combining commercial credibility with the leadership maturity required to elevate the team.

Briefing to signing of contracts was completed in approximately 8 weeks.