Key Questions to Ask When Hiring a C-suite Executive in Tech

Asking the right interview questions when looking to hire a C-suite executive for your tech startup team is important for narrowing down candidates to find your unicorn fit. Betts Recruiting has put together these question lists – developed from our years of executive search experience – to help you zero in on candidates who not only bring the technical understanding required in the SaaS market of today, but who also embody the strategic mindset needed to help scale your go-to-market (GTM) strategy and launch you into the next round of funding.

Interviewing and Hiring C-Suite Executives for Tech Startups

The reigning talent acquisition practices and solutions in the technology space are not always built to handle modern sourcing goals, let alone help you find the right fit in a sea of experienced – and not so experienced – candidates. The post-pandemic world has brought new challenges to the SaaS sector, including tighter software spending budgets, growing data privacy concerns and an increasingly skeptical customer base. C-suite executives in tech must navigate these hurdles while also wearing multiple hats for the greater team, especially in early-stage startups.

For a more in-depth dive into the top questions to ask for any of these positions, check out our previous blogs here:

• Key Questions for Interviewing a Tech CEO
• Key Questions for Interviewing a Tech CRO
• Key Questions for Interviewing a Tech CMO

Chief Executive Officer (CEO)

A tech startup’s CEO serves as the primary leader and strategic visionary, responsible for steering the company’s overall direction, securing funding and building a strong organizational culture. Their role varies significantly between funding stages, from having to fill in for different executive and managerial titles in early-stage startup environments to focusing more on strategic leadership and stakeholder management as the company grows.

Chief Marketing Officer (CMO)

The CMO of a SaaS startup acts as the steward of client relationships and engagement, promoting brand trust while ensuring effective communication that speaks directly to customers’ needs. They must balance data-driven decision-making with creative strategy, particularly crucial in early-stage startups where establishing credibility with target audiences is paramount.

Chief Revenue Officer (CRO)

A venture-funded startup’s CRO drives revenue growth by aligning sales, marketing and customer success teams while ensuring their go-to-market strategy and sales motion positions the company for success. Their role evolves from hands-on selling in early stages to implementing scalable processes and managing diverse revenue streams as the organization grows.

Interview Questions for C-Suite Candidates

Below, we outline the key questions that help you as a hiring manager evaluate a candidate’s track record, strategic approach and problem-solving abilities when applied in a fast-paced startup environment. These questions are primarily divided into two sets: those that explore the candidate’s past experience as it relates to the role they are interviewing for, and those that test their critical thinking with hypothetical situations. 

Questions About Past Roles & Responsibilities

These questions are meant to highlight the candidate’s previous professional experiences, responsibilities and role-based proficiencies, and outline their methodologies and processes in leadership. While there are common areas of assessment across the C-suite titles featured here, specific inquiries must focus on the particulars of their respective positions, getting into the strategic and tactical aspects of their leadership history.

Shared C-suite Executive Questions

1. Past Executive Experience: Past experience in a previous executive role is an increasingly important requirement in tech, with most startups seeking a candidate who occupied a similar C-level position for years before. Ask for a detailed job history and dive into previous leadership positions they have held, and inquire directly about how they relate to the title they are interviewing for.
2. Team Development: When assessing executive candidates’ ability to build and lead teams, you will want to explore their specific approaches to building out their teams and how they factor Cost-per-Hire and revenue targets into their recruiting decisions. Ask for examples of successful team building and clear methodologies for identifying top performers.
3. Strategic Planning & Execution: Have the candidate describe their approach to organizational planning and goal setting, as well as how they track how their team performs based on their targets. Look for leaders who can demonstrate a clear link between strategic thinking and measurable outcomes, with specific examples from their past experiences.

CEO

1. Hiring Leadership: A CEO candidate needs to be able to help your org find the right talent to lead each team and ensure that the company scales overhead with revenue growth successfully. Ask them how they would recruit for new executive positions as your firm grows and what they would look for in the right fit to lead a given team.
2. Stakeholder Management: Chief Executive Officers in a startup environment must be able to successfully navigate relationships with multiple stakeholders both externally and internally. Ask the candidate to outline their approach to engaging with investors, board members, team leaders, customer points of contact and other representatives from key audiences, and evaluate how their responses align with what you are looking for in your org’s representative.
3. Performance Tracking: Let the candidate provide their methodology for setting and tracking organizational performance goals, including what key metrics they watch and how they hold each team accountable for their targets. Also ask them to point to past experiences that have informed their current thinking on this and give examples of how they have demonstrated success.

CMO

1. Brand Management: Ask your candidate how they have approached branding at all levels as a marketing leader, and how they have leveraged input internally balanced with analytical data to refine the brand’s story. Their history should include successful brand transformations that demonstrate their ability to reinvent market positioning.
2. Leveraging Analytics: Have the candidate describe how they have approached marketing analytics in previous leadership positions and give an example of successfully leveraging KPIs to drive goals. Look for someone who demonstrates the ability to adapt based on data without disrupting ongoing campaigns.
3. Channel Strategy: Ask your CMO candidate to provide examples of how they have balanced leveraging different marketing channels, including how they prioritized any based on resources or time required. You will want to evaluate their ability to create a comprehensive multi-channel strategy, as well as their knowledge of your market audience and which channels they consume the most.

CRO

1. Sales Forecasting: Understanding a CRO candidate’s approach to forecasting and pipeline management is crucial to vetting their experience. Explore how they have implemented processes to ensure accurate predictions, and ask what they did to maintain team accountability and drive growth.
2. Customer Retention: Discuss the candidate’s track record in managing and improving customer retention. Evaluate their methods for reducing churn and creating opportunities for revenue expansion.
3. Revenue Forecasting: Have them detail their approach to forecasting and pipeline management. The candidate should demonstrate clear processes for ensuring accurate predictions and maintaining accountability. Look for examples of successful forecast management.

Situational Questions for C-Suite Candidates

Situational questions give you a look into a candidate’s thinking and help illustrate how they respond to the type of challenges that will inevitably occur in executive leadership. Focus on scenarios and situations where the candidate can demonstrate their ability to problem-solve and work with both internal and external stakeholders to drive success. These questions help assess the candidate’s adaptability, decision-making abilities, and strategic thinking to see if they can be a good fit for your executive team.

Shared Questions

1. Crisis Management Present candidates with complex scenarios involving market disruption or internal challenges. Pay attention to how they approach strategic response development and demonstrate leadership during uncertainty. Look for balanced thinking that considers both immediate needs and long-term implications.
2. Resource Optimization Evaluate your candidate’s ability to maintain performance under constraints by presenting scenarios involving budget cuts or resource limitations. Listen for innovative approaches to resource allocation and strategies for maintaining team morale during challenging periods.
3. Team Vision: Ask the candidate to describe what they would do in the first 90 days in their new role and how they would make sure their teams are aligned with their goals. Follow up with additional questions on how they would navigate internal challenges and communicate with their team members, looking for any demonstrations of the soft skills they are able to bring to the table for your C-suite.

CEO

1. Culture & Communication: Explore how the candidate would foster cultural alignment in growing teams, including their methods for ensuring clear communication and reinforcing organizational values as the company continues to expand. Listen for strategies involving demonstrable empathy and proactive team engagement that gets ahead of the potential gap between teams as your workforce grows.
2. Sales Motion Adaptability: Ask your CEO candidate how they would handle a situation where your product seems misaligned with your market base after recent changes. The ability to make strategic adjustments in such scenarios is a key indicator of adaptability.
3. Technology Strategy: Present a scenario involving a new technology hitting the market that could benefit your GTM teams. Look for candidates demonstrating the ability to balance the long-term and short-term impacts of implementing new solutions into your tech stack versus their scalability for your go-to-market operations and costs.

CMO

1. Lead Gen Growth: Create a scenario requiring doubled lead generation without additional resources. The candidate’s provided approach to diagnosing and reversing metric declines will help give you valuable insight into their problem-solving abilities.
2. Brand Evolution: Present a scenario where the CEO or board requests a significant brand overhaul based on changing market conditions. Look for their ability to balance stakeholder demands with strategic brand management.
3. Competitive Disruption: Ask your CMO candidate to describe how they would handle a competitor cutting into your market share. See how they approach reviewing and addressing this threat, and how they see marketing’s role in countering it.

CRO

1. Revenue Diversification: Present a scenario where the CEO or board asks your candidate to look into developing new revenue streams to offset expected losses. Pay attention to how they balance existing business with pursuing new opportunities.
2. Performance Turnarounds: Create a scenario where current sales processes are following short of forecasted targets. Look for candidates that can demonstrate a systematic approach to diagnosis and implementation of solutions.
3. Compensation Structuring: Describe a scenario where the current sales compensation structure is being revamped. How would they approach redesigning it to align with your developed sales motion while ensuring fair and motivating incentives?

Find the Right C-suite Executive with Betts Recruiting

Recruiting top-tier leadership talent is crucial for your company’s growth, and finding the right C-suite executive requires deep market expertise. Betts Recruiting specializes in connecting tech startups with proven leaders who can drive revenue, scale operations, and position your company for long-term success.

Contact Betts here to start your search for the perfect CEO, CMO, or CRO who will take your company to the next level.