Overcoming SaaS Executive Search Challenges | How Oakstone International Delivers Results

12 Dec

Software as a Service (SaaS) can be high-growth, complex, and competitive, which means finding the right people to meet the unique requirements is rarely straightforward.

At Oakstone International, we partner with SaaS, technology, and growth-led organisations to find the people they need. We're exploring some of the most common executive search pain points hiring teams face and how Oakstone consistently overcomes them to deliver long-term, high-impact hires.

Have you faced any of these challenges?

Finding Leaders with the Right Revenue Scale Experience

One of the most common challenges in finding senior-level revenue leaders is identifying candidates who have owned the right level of revenue responsibility. Too often, candidates look strong on paper but lack experience operating at the scale required, whether that's taking a business from £5m to £20m ARR or building repeatable GTM engines in complex environments.

How Oakstone Overcomes Finding Leaders with the Right Revenue Scale Experience

We go beyond job titles and surface-level metrics. Our consultants qualify candidates on:

The scope of revenue ownership
The complexity of the go-to-market motion
Stage-of-growth alignment

Here is an example of how Oakstone found the right person with the right revenue growth experience for Didomi.

Understanding the right level of experience ensures candidates are not just successful but successful in the right context for the companies we are working with.

Brand Perception & Low Market Awareness

For SaaS and technology businesses operating across regions and stages, brand perception is often a challenge.

Challenges often arise when:

The company is well established in one core region but largely unknown in a new geography where it is hiring.
Growth plans, funding milestones, or strategic pivots are not yet visible externally.
The brand is misunderstood, mispositioned, or associated with an outdated narrative.

For SaaS companies expanding internationally, this is especially common. A business may have strong product-market fit and customer traction in its home market, yet little to no awareness among senior talent in a new region. In these cases, the role and the company must be actively sold to candidates, not assumed to speak for themselves.

Similarly, more established or long-standing organisations can face a different but equally challenging issue: legacy brand perception. The external market may still associate the company with:

An earlier stage of growth
A previous leadership team
An outdated product, culture, or pace of innovation

Even when the company has changed significantly, candidate perception often lags. This inaccurate perception can impact senior-level attraction, particularly among high-calibre executives who are selective about brand, trajectory, and risk.

How Oakstone Overcomes Brand Perception & Low Market Awareness

Oakstone is able to reposition narratives by accurately presenting opportunities to candidates. We act as an extension of our partners' leadership teams, ensuring candidates fully understand not only what the company is today but also its future growth plans. This includes clearly articulating:

The strategic ambition behind the hire and why the role exists now
The future-state opportunity and the executive's influence on shaping it
The investment thesis, growth trajectory, and leadership intent

Here is an example of how we overcame perception issues for SugarCRM and Totara. When market awareness is low or outdated, we proactively educate and reframe a more current, accurate picture of the company.

Accurately positioning the company leads to stronger candidate engagement, higher-quality shortlists, and leaders who are aligned with the company's true direction.

Location Constraints in a Global Talent Market

Strict location requirements can dramatically reduce the pool of potential candidates, particularly for senior, highly specialised roles. This is a challenge Oakstone International frequently encounters when partnering with scaling SaaS and technology businesses or companies that are located outside of large cities but still have an in-office work requirement.

How Oakstone Overcomes Location Constraints in a Global Talent Market

Oakstone's search methodology is designed to identify and engage the right leaders in specific regions, rather than relying on generic global networks. We combine deep functional expertise with granular regional intelligence.

Oakstone assisted Tekion with hiring in specific regions in the USA.

Evolving Role Requirements & Ambiguity

In high-growth businesses, role briefs often evolve mid-search as priorities shift or new insights emerge. This can be challenging for internal and external search teams.

How Oakstone Overcomes Evolving Role Requirements & Ambiguity

We build flexibility into every engagement. Through continuous calibration, we:

Re-align candidate profiles in real time
Test requirements against market feedback

This reduces false starts and accelerates confident decision-making.

During Oakstone’s search for COO at Amici Procurement, the ideal profile evolved multiple times through the search. We adapted quickly to changing expectations without disrupting candidate experience or momentum.

Assessing Cultural Fit Beyond the CV

Cultural misalignment is one of the most common reasons executive hires fail, particularly in scaling organisations, where teams rely on strong collaboration. Assessing cultural fit can be challenging when reviewing CVs alone.

How Oakstone Overcomes Evolving Role Requirements & Ambiguity

Our assessment process goes far beyond CVs and track records. We have conversations with every candidate to evaluate:

Leadership style and values
Team dynamics and collaboration
Change resilience and adaptability

This ensures candidates are a good fit for the organisation and that the organisation is a good fit for the candidate.

Company Size & Stage Alignment

A candidate can be exceptional and still be wrong for the business at a particular moment in its growth journey.

A profile required at Seed stage is fundamentally different from what is needed at Series A, Series B, or beyond to reach the next stage. Someone who excels at building from zero, operating without structure, and wearing multiple hats may not be the right leader to introduce process, scale teams, and professionalise functions at the next stage of growth. Equally, executives who have thrived in later-stage or enterprise environments often struggle in early-stage, resource-constrained businesses where ambiguity is high, and support is limited.

Misalignment at any level can stall growth and result in costly mis-hires.

How Oakstone Overcomes Company Size & Stage Alignment

Oakstone rigorously assess when and in what context candidates have achieved. This includes evaluating:

Experience aligned with the company's current stage.
Evidence of achievement aligned with the hiring company's requirements
Comfort with the balance between strategic leadership and hands-on execution

This dramatically improves long-term retention and impact.

Just as importantly, we work closely with founders, boards, and leadership teams to clarify what the business truly needs.

Oakstone assisted Tealium in hiring an SVP GM EMEA, where there were challenges targeting individuals from similar sized backgrounds as Tealiums. Discover how we overcame the challenge here.

Complex Products, Verticals & Niche Skill Sets

Executive searches involving complex products, specialist verticals, or highly niche skill sets are among the most challenging to execute effectively, as they require a deep understanding from the recruiter.

Candidates may appear relevant on paper, but without deep qualifications, it can be challenging to determine whether their experience is truly transferable or simply adjacent.

Finding the right person often requires more time and deeper engagement with each candidate to understand their previous experience with similar products, buyers, and sales cycles. This level of assessment is essential, particularly when a mis-hire can slow momentum or damage credibility with customers.

How Oakstone Overcomes Complex Products, Verticals & Niche Skill Sets

Our approach allows us to:

Speak the language of candidates credibly, enabling more meaningful and technically informed conversations.
Spend the necessary time qualifying experience, knowledge, and decision-making depth.
Distinguish between genuine subject-matter expertise and surface-level exposure.
Identify transferable experience that others may overlook.

Rather than relying solely on keyword matching or assumptions, we assess depth rather than familiarity. This ensures candidates are not only capable of operating within complex environments but can add value quickly and confidently.

Rootstock had previously struggled to find the right fit VP of Sales, due to the complexity of their product and vertical. Read how Oakstone assisted them.

Overcoming Role History & Reputation Challenges

Roles that have been filled in the past and not worked out, or companies that carry reputational baggage, present a unique challenge in executive search. At the senior level, candidates are highly attuned to risk and will question why a role is vacant again, what went wrong previously, and whether the underlying issues have genuinely been resolved.

In these situations, there is often an increased perceived risk from the candidate's perspective. Without the right context, experienced executives may assume:

The role lacks clarity or authority
Internal alignment is weak
Structural or leadership issues remain unresolved

Similarly, companies with reputational challenges often find that senior candidates approach opportunities with caution. This makes it essential not just to present the role but to articulate the why behind it clearly.

Without in-depth conversations, it may be challenging to attract candidates and overcome perceived reputations.

How Oakstone Overcomes Overcoming Role History & Reputation Challenges

We don't attempt to gloss over history or oversell the opportunity. Instead, we focus on transparency and context. By doing so, we:

Get to know the company, role and hiring manager, as well as what has changed structurally, strategically, or culturally, so we can articulate the role accurately to potential candidates.
Reframe the lessons learned from previous hires, explaining what the experience revealed rather than avoiding it.
Provide candidates with a clear rationale for why the role now exists, and why it is set up for success this time.

At executive level, credibility matters more than polish. By answering difficult questions upfront and providing a compelling, evidence-based 'why,' Oakstone reduces perceived risk and enables candidates to make confident, informed decisions.

During our search for an SVP Sales for Icertis, we faced challenges with reputation, but we overcame them by positioning their future commitment to improvement.

Urgent, Volume & Logistical Complexity

For companies hiring for multiple roles simultaneously, there can be significant time pressures and logistical complexities.

Challenges typically arise when:

Interview processes involve numerous stakeholders across functions, regions, or time zones
Decision-making urgency clashes with leadership availability

At the executive level, delays, poor coordination, or inconsistent communication can slow hiring and actively damage credibility and reputation. High-calibre candidates are acutely aware of process quality and will often disengage if momentum is lost or the experience feels disorganised.

How Oakstone Overcomes Urgent, Volume & Logistical Complexity

We ensure every part of the process moves efficiently without compromising assessment quality or candidate experience. This includes:

Seamless interview coordination across multiple stakeholders, regions, and time zones
Clear, consistent communication that keeps both clients and candidates aligned at every stage
Proactive momentum management to prevent bottlenecks.

We protect the candidate experience and candidate clarity, pace, and professionalism. Oakstone ensures candidates remain engaged, informed, and confident in the process.

Oakstone assisted Tekion with the logistical complexity of managing interviews for over 70 candidates across 18 roles required. This included scheduling interviews for panels of 7-8 stakeholders and efficiently managing calendars.

Are you facing any of these challenges and are looking to hire GTM or executive leadership talent? Speak to Oakstone International

Contact Oakstone