CRO

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Hiring a CRO

Experience Profile (Been There/Done That)

(prioritized)

  1. Scale-up experience: Has been through same journey (ex: $20M to $100M)
  2. Motion: Has led organization with same target motion (new vs expansion; if new, self sourced vs. SDR sourced vs. inbound vs. PLG vs. channel vs. …; similar licensing model – ex: seats vs. consumption vs. etc.)
  3. Deal size: Has sold with same deal size/complexity (typically by order of magnitude of ACV – $1K / $10K / $100K / $1M / …)
  4. Geo: Has led teams selling into same geographies as where you current operate/intend to operate in within the next 2 years.
  5. Culture Fit / Exec. Traits: Strong culture fit. For example, comfortable with conflict/directness if applicable
  6. Functional Breadth: Prior experience running the following if applicable: post-sale/CS; RevOps; Enablement; Marketing
  7. Industry: Has sold into target industry (this knowledge is harder to impart)
  8. Product/Persona: Has sold into target product category (easier to teach/learn); this is the same as/similar to having sold into a particular job function/persona; also the same as/similar to having sold ‘need to have’ vs ‘nice-to-have’ products or having sold mature versus emerging, category-creating products.

Resources

CRO Interview Guide and Scorecard

Below is a comprehensive interview scorecard tailored for hiring a Chief Revenue Officer (CRO) in a B2B SaaS startup.

Guiding Principles & Other Considerations:

  • Rely on backchannel reference checks to (a) confirm key skills and traits and (b) evaluate all yellow & red flags.
  • Clarify candidates’ actual roles and responsibilities as they tend to exaggerate. Were they a direct or dotted-line manager? Did they conceive, lead, or merely support key initiatives they reference?
  • Probe for specificity and detail
  • Ask anthropological (tell me about a time when you…) rather than aspirational (how would you…) questions
  • Do not lead the candidate by asking . For example, don’t ask, ‘Tell me about your approach to recruiting outstanding passive candidates.’  Rather, ask questions that are one or two levels up in abstraction.  For instance, ‘What is your approach to hiring?’ or more generally, ‘What is your approach to Talent?’
  • Revenue leaders should have rigorous but flexible routines – ‘a playbook written in pencil rather than pen’

1. Track Record

a. Purpose

To assess the candidate’s history of achieving revenue targets in similar environments.

b. Interview Questions

  1. Describe the ICP and persona you targeted at your most recent employer.  What sales motion(s) did you rely on to generate demand?
    • Probe to verify the candidate has a strong grasp of the unique success factors and challenges of selling to your target buyer.
    • Look for alignment with your target ICP and persona as well as with your motion (PLG; inbound marketing-led; SLG; channel-led; etc.)
  2. Which revenue functions did you directly lead at your most recent employer? How large was the organization you led?
    • Probe for depth of knowledge in the functions you are hiring them to lead: new business sales; expansion sales; sales engineering; customer success / technical account management; revenue operations; revenue enablement; marketing; etc.
  3. What was the starting and ending ARR during your tenure leading sales at your most recent former employer? What were one or two initiatives you directed that unlocked significant growth?
    • Assess alignment with your expected growth over the next 4 years (ex: $10M to $100M).
  4. In which geographies did you directly lead revenue teams?
    • Probe for country-level nuances especially if expecting the candidate to drive expansion into new locales
  5. What were your team’s bookings targets in each of the last 2 years?  What percentage of target did you achieve?
    • Look for the candidate to have these numbers committed to memory. The numbers should be precise (ex: 108% of plan).  Seek a record of consistent overachievement.

c. What to Look For

Consistent overachievement of targets in similar environments (ASP, sales motion, buyer, industry, geography, ARR scale). Specific examples and quantifiable results.

d. Scoring Criteria

  • 5 (Excellent): Proven track record of exceeding targets in very similar environments. Demonstrates deep understanding of the target market and sales motion. Quantifiable results and specific examples provided.
  • 3 (Average): Some alignment with the company’s go-to-market approach and ASP but lacks depth or direct experience in one or more critical areas (e.g., geography or buyer persona).
  • 1 (Poor): Limited or no relevant track record in similar B2B SaaS contexts, with minimal success metrics or clarity.

2. Team Building

a. Purpose

To evaluate the candidate’s ability to build, develop, motivate, and retain high-performing revenue teams, including a track record of developing star reps and managers, effective organizational design, and strong communication and motivational skills.

b. Interview Questions

  1. Walk me through your approach to hiring top talent. Tell me about the best person you ever hired.
    • Look for methodical recruitment and talent selection processes.
    • Look for the candidate to name top reps and managers they take pride in having recruited and developed.
  2. Tell me about a time you had to replace an underperforming manager or rep.
    • Look for decisiveness, fairness, and coaching abilities.
  3. How did you approach people onboarding and ongoing training at your most recent employer?  What worked well? What would you change?
    • Look for a structured approach to onboarding and ramping new hires.
    • Assess their ability to think critically about how to improving revenue enablement.
  4. What changes to the organizational structure and to roles & responsibilities did you make at your most recent employer? Why did you make those changes?  What was the impact?
    • Look for a structured approach to organizational design and a strong grasp of change management.
  5. Tell me about a time you kept your sales team motivated in a challenging market.
    • Assess communication style and motivational strategies.

c. What to Look For

Evidence of building and scaling successful sales teams, developing talent, and fostering a positive and productive team culture.

d. Scoring Criteria

  • 5 (Excellent): History of building and leading high-performing teams with a track record of developing talent. Clear articulation of a disciplined hiring approach and strong leadership skills.
  • 3 (Average): Some success in team building but may lack consistency, scalability, or clear frameworks for hiring and development.
  • 1 (Poor): Limited examples of successful team development. High turnover under their leadership.

3. Strategic Planning & Execution

a. Purpose

To assess the candidate’s ability to develop and execute effective revenue strategies.

b. Interview Questions

  1. Describe the process you used for market segmentation and territory planning at your most recent employer.
    • Look for methodical territory design aligned with overall strategy.
    • Look for data-driven insight and strategic thinking.
  2. Walk me through the compensation plan(s) you that were in effect at your most recent employer.  What adjustments did you make to plan(s)?  Why? What impact did those adjustments have?
    • Look for a deep understanding of compensation plan mechanics across multiple functional roles
  3. Tell me about a major pricing or packaging change you were involved with — how did you execute it? What was your specific role?
    • Explore their experience with pricing strategy and change management.
  4. Tell me about your GTM strategy when a prior employer launched a new product? What was your specific role?  What worked? What did not work?
    • Look for concrete strategic thinking that covers people, process, and technology as well as well-managed execution
  5. Tell me about a time when you had to make a significant change to your go-to-market strategy. How did you manage the transition?
    • Evaluate adaptability and resilience.
  6. Describe the process you use to develop a yearly or quarterly revenue plan.
    • Assess their ability to set objectives, allocate resources, and define KPIs.

c. What to Look For

Strategic thinking, analytical skills, and the ability to translate strategic plans into actionable execution plans with a strong emphasis on change management.

d. Scoring Criteria

  • 5 (Excellent): Demonstrates deep insight and a track record of executing complex revenue strategies with strong outcomes, including handling pivots successfully.
  • 3 (Average): Shows some strategic thinking but may lack sophistication or a consistent track record in change management and complex planning.
  • 1 (Poor): Provides vague or generic responses, with limited evidence of strategic planning or execution ability.

4. Operational Rigor

a. Purpose

To assess the candidate’s ability to implement and manage effective sales processes and operations.

b. Interview Questions

  1. In deep detail, describe the operating rhythm you ran at your most recent employer – the frequency and format of various meetings and processes.
    • Look for structure, detail, consistency, and clear accountability.
  2. At your most recent employer, what was your approach to quota setting?
    • Look for a data-driven and fair approach.
  3. What was the forecast accuracy goal at your most recent employer? What was your actual forecast accuracy?  What initiatives did you lead to improve forecast accuracy?
    • A great answer includes: “Our goal was to be within +/- x% on Day y of the quarter.”
    • Gauge their methodology and tools used (e.g., CRM hygiene, pipeline reviews).
  4. Walk me through the stage-by-stage sales process at your most recent employer. What adjustments, if any, did you lead during your tenure?
    • Understand their process optimization skills.
    • Listen for definition and enforcement of verifiable exit criteria.
  5. Which methodology did you use for deal qualification and opportunity health inspection at your most recent employer? How did your team leverage this methodology?
    • Listen for selection of a sales motion appropriate methodology (ex: MEDDICC for Enterprise sales or BANT for SMB).
  6. What strategies did you apply to manage discounting at your most recent employer?
    • Explore their approach to pricing discipline and value selling.

c. What to Look For

Systematic approach to forecasting and pipeline management Strong understanding of sales operations, data-driven decision-making, and a focus on process improvement.

d. Scoring Criteria

  • 5 (Excellent): Highly disciplined in operational practices, with detailed examples of accurate forecasting, well-defined processes, and success in optimizing sales cycles.
  • 3 (Average): Some structure in operational discipline but may lack consistency or proven track record in significantly improving processes or forecast accuracy.
  • 1 (Poor): Chaotic or ad-hoc approach with little evidence of establishing a strong revenue operating rhythm.

5. Financial & Analytical Acumen

a. Purpose

To assess the candidate’s ability to manage budgets, analyze data, and use insights to drive decision-making.

b. Interview Questions

  1. Describe how you built the capacity plan for the revenue organization at your most recent employer.
    • Listen for close collaboration with the Finance team.
    • Gauge how they balance growth objectives with cost controls.
    • Assess their understanding of staffing ratios for sales to sales support roles
  2. What are your top sales and revenue KPIs?  What dashboards and reporting did you rely on at your most recent employer?
    • Look for an understanding of leading vs. lagging indicators.
    • Evaluate familiarity with BI tools.
  3. Describe a time you used data or analytics to solve a critical revenue challenge.
    • Look for data-driven problem-solving skills.

c. What to Look For

Strong analytical skills, understanding of key financial metrics, and the ability to use data to make informed decisions. Experience working closely with finance teams to align revenue and financial goals.

d. Scoring Criteria

  • 5 (Excellent): Demonstrates expert understanding of financial metrics, budgeting, and analytics, with a proven record of data-driven revenue growth.
  • 3 (Average): Some financial and analytical understanding but may lack a systematic approach to using data for strategic decisions.
  • 1 (Poor): Minimal evidence of financial acumen or data-driven decision-making; focuses on anecdotal rather than analytical approaches.

6. Cross-Functional Collaboration

a. Purpose

To assess the candidate’s ability to work effectively with other key partners within the organization.

b. Interview Questions

  1. How did you work with Marketing at your prior employer?  Tell me about a misalignment you had with Marketing? How did you resolve it?
    • Look for an integrated demand generation approach spanning account prioritization & targeting, coordinates campaigns, etc.
    • Look for frequent, structured communication between Sales & Marketing
  2. How did you work with Product at your prior employer?
    • Look for the candidate to describe processes for and examples of working closely with Product to influence the roadmap based on customer, pre-sales, and post-sales feedback.
  3. How did you work with Finance at your prior employer?
    • Understand their approach to budget and revenue planning collaboration.
  4. Give me an example of a time you had to resolve a conflict between sales and another department.
    • Evaluate conflict resolution and relationship management skills.

c. What to Look For

Strong communication and interpersonal skills, ability to build relationships, and a collaborative approach.

d. Scoring Criteria

  • 5 (Excellent): Consistently demonstrates outstanding collaboration with multiple stakeholders, actively aligning cross-functional teams for shared success.
  • 3 (Average): Able to work with other departments but may lack proactive collaboration or struggle with conflict resolution.
  • 1 (Poor): Little evidence of successful cross-functional projects or alignment; operates in isolation.

7. Large Deal Execution

a. Purpose

To understand the candidate’s expertise in orchestrating and closing large, complex B2B SaaS deals, including negotiation, stakeholder management, and deal strategy.

b. Interview Questions

  1. Tell me about the largest or most complex deal your team closed at your previous employer.
    • Look for details on deal size, complexity, timeline, and challenges.
  2. For that deal, who were the key people on the customer side? What were the roles of various people on your team?  What was your role?
    • Look for details on names and roles. Understand their approach to executive alignment and champion building.
  3. For that deal, please expand on the details of the negotiation.
    • Assess strategic negotiation skills, value-based selling approach, and understanding of tradeoffs in pricing and in terms & conditions.
  4. For that deal, what tactics did you use to accelerate the sales cycle?
    • Look for resource orchestration, process optimization, project-management, and relationship-building strategies.

c. What to Look For

Proven track record in closing large ARR deals. Experience with complex sales cycles, strong negotiation skills, and the ability to build and maintain relationships with key stakeholders.

d. Scoring Criteria

  • 5 (Excellent): Detailed examples of closing large, complex deals with strategic negotiation skills and effective internal orchestration.
  • 3 (Average): Some experience with larger deals but may lack a robust methodology or repeatable approach.
  • 1 (Poor): No substantial experience with enterprise-level deals or struggles to articulate a coherent large-deal playbook.

8. Culture & Values Alignment

a. Purpose

To ensure the candidate’s personal values, leadership style, and vision align with the company’s culture, fostering a positive environment and long-term fit.

b. Interview Questions

  1. What motivates you personally and professionally?
    • Look for alignment with the company’s mission and values.
  2. Describe the culture you strive to create within your teams.
    • Assess whether this culture complements the broader organizational culture.
  3. Tell me about a time when you had to handle an ethical dilemma or gray area on your team, with a deal, or at a customer?
    • Explore their integrity and ethical decision-making.
  4. What are your non-negotiable principles as a leader?
    • Understand the candidate’s core values.
  5. How do you nurture diversity, equity, and inclusion within your organization?
    • Look for actionable strategies, not just lip service.

c. What to Look For

Alignment with the company’s mission, vision, and values. Demonstrates a positive attitude, strong work ethic, and a collaborative spirit. Look for examples of behaviors that reflect the company culture (e.g., innovation, customer focus, integrity).

d. Scoring Criteria

  • 5 (Excellent): Strong alignment with company values, demonstrates integrity, empathetic leadership, and a clear commitment to building an inclusive, high-performance culture.
  • 3 (Average): Generally aligned with company culture but may not have a fully developed philosophy or demonstrated track record in values-driven leadership.
  • 1 (Poor): Significant misalignment with core values or evidence of past leadership behaviors that conflict with the desired culture.

How to Use This Scorecard

  1. Pre-Interview Preparation: Share these sections among interviewers so each person can focus on specific areas.
  2. Structured Note-Taking: During the interview, use each section’s questions as a guide, capture candidate responses, and assess them against the “What to Look For” notes.
  3. Final Scoring: After the interview, rate the candidate in each category (5, 3, or 1). Consolidate scores across all interviewers to get an overall assessment.
  4. Decision Process: Compare the candidate’s scores to any internal benchmarks or weighted criteria. Use the insights to make a hiring decision that balances track record, cultural fit, and strategic alignment.

This scorecard ensures a robust, consistent evaluation of each candidate’s capabilities and alignment with your company’s goals and culture.

The First 90 Days for a New CRO/VP of Sales

0 to 3030 to 6060 to 90
Alignment– Align with your CEO on key objectives & scope of control​
– Build a relationship with the CMO by understanding our marketing strategy, campaigns, program performance, etc.		– Prepare for your first Board meeting​
– Define leading & lagging KPIs and targets​
– Deepen partnership with CMO		– Lock down your top 3-5 strategic initiatives​
– Present your strategic plan and latest results to the Board​
– Deepen partnership with CMO
Culture– Walk the walk on your values​
– Never speak ill of your predecessor		<—<—
Customers– Identify and meet with top strategic customers​
– Align with your CPO to understand the product, value prop., & roadmap		– Gain a deep insight into win/loss​
– Engage on top new logo deals​
– Identify and meet with top at-risk customers		– Continue to engage on top new logo deals and to meet with customers
Pipeline & Process– Identify the top 5 deals you can impact​
– Understand the current sales process & operating rhythm​
– Don’t assume the playbook from your prior company will work at your new one		– Engage the team on the top 5 deals​
– Understand where deals stall/die​
– Tune your competitive messaging & motion​
– Roll out operating rhythm updates for 1:1/deal reviews & forecasting		– Roll out sales process updates​
– Control discounting (if applicable)
Talent– Align with your CFO on the sales budget & capacity (plan vs. actual)​
– Assess each level of your organization to identify top & bottom performers​
– Hire known closers from your network		– Ensure you have recruiting capacity and hiring processes to meet your plan​
– Remove low performers​
– Determine key enablement needs​
– Hire in the image of your best players		– Launch critical enablement programs​
– Continue hiring top-talent​
– Recognize and reward your top players
Note: Though you can craft strategy, you are unlikely to complete the following in the first 90 days: (1) change the product, (2) overhaul pricing, (3) enter a new industry, geography, or size segment, (4) Implement new technology, (5) change sales compensation

SaaS CRO Compensation

  • CROs are typically on 50/50 base/variable plans but can range to 65/35
  • CRO compensation should be closely aligned with the executive team as well as with the overall revenue team. To that end,
    • Executive Team Alignment: CRO net new ARR target should match the company target. The company target is usually 10%-20% lower than the total quota deployed to account executives. (The Board target is usually an additional 10%-20% below the company target). CRO and CMO plans should have high overlap to ensure alignment.
    • Revenue Team Alignment: CRO plan mechanics (metrics, payment frequency, accelerators, etc.) should match those of AEs and sales leaders. The CRO may have additional measures, ex. sales efficiency, but additional measures should complement and not be in conflict with those of the revenue team.
  • Variable compensation metrics
    • Net new ARR = new logo + expansion – downgrade – churn
    • Efficiency/Profitability
      • Sales efficiency = (sales expense) / (net new ARR)
        (or similarly, CAC payback or LTV/CAC)
      • FCF Margin or EBITDA margin
      • NRR and/or GRR (though technically part of net new ARR)
PercentileOTE ($)Equity (%)
25th$450,0000.75%
50th$550,0001.0%
75th$625,0001,5%
Source: Insight Partners; Sept. 2023; Company ARR from $10M to $100M

CRO Severance

EntitlementTypicalGenerousExceptional
Base salary3 mos6 mos3 mos for every year of service; min 3 & 12 mos
Variable1none2pro-rated bonus based on bookings3Greater of (a) pro-rated bonus based on bookings (b) pro-rated bonus based on time4
HealthcareCash to cover 3 mos COBRACash to cover 6 mos of COBRACash to cover 3 mos of COBRA for every year of service; min 3 & 12 mos
Accelerated vesting if termed under 12 mosnonenoneprorated and adjusted vesting5
Double-trigger acceleration6noneyesyes

Notes:

1 CROs usually receive a performance based bonus and are therefore not on true “commission” plans. Commission plans are only common for early stage startups where the CRO is a 1st line sales leader.

2 If the CRO were on a true commission plan rather than a bonus plan, then in most jurisdictions, they would need to be paid for commissions earned as of termination date

3 Example of pro-rated bonus based on bookings: CRO has quarterly bookings target of $5.0M. Leaves on calendar day 63 of 90 days quarter with $2.0M booked. Hence, they would receive 40% (2/5) of their target bonus for the quarter.

4 Example pro-rated bonus based on time: CRO has quarterly bookings target of $5.0M. Leaves on calendar day 63 of 90 days quarter with $2.0M booked. Hence, they would receive 70% (63/90) of their target bonus for the quarter.

5 Pro-rated and adjusted vesting example: CRO leaves 63 days into Q3; thus, their tenure is 153 days. Adjustment factor of 50%. If they had 10,000 options that vest over 4 years and a typical 1 year ‘cliff,’ then they would be eligible for: (10,000) x [153 / (365*4)] * 50% = 524 shares.

6 “Double-trigger acceleration upon separation following a change of control” means that an employee’s unvested stock options or shares will immediately vest if two events occur: a change in company ownership (change of control) and then the employee is terminated without cause shortly after (often 12-18 month) that change of control.

When Should CMO Report to CEO vs. CRO?

AttributeReport to CEOReport to CRO
Dominant GTM StrategyMarketing-led; BalancedSales-led
Marketing focusBrand building (long-term)Demand Generation (short-term)
StageEarlyMid-to-Late
Growth RateHighModerate-to-Low
Product PortfolioComplexModerate-to-Low
Importance of investor & analyst relationsHighModerate-to-Low
ABM-focusLow-to-ModerateHigh

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