How do I find a good sales leadership coach for my VPs of Sales and Marketing?

For VPs of Sales and Marketing, I’d look for an executive coach with real revenue-organization operating experience, not a generic leadership coach. The distinction matters: at that level, the coach should be able to challenge strategy, leadership behavior, cross-functional dynamics, and operating cadence—not just work on “executive presence.”

What I’d screen for

• Has actually operated at VP/CRO/CMO level. Ideally they have personally led a revenue organization, not just coached one.
• Has coached leaders at your company’s stage. A coach experienced with Fortune 500 executives may be a poor fit for a $20M growth company, and vice versa.
• Understands Sales + Marketing alignment. For your situation, I’d favor someone who can work across ICP, positioning, pipeline, forecasting, demand generation, handoffs, and executive-team dynamics.
• Situation-led rather than curriculum-led. The coaching should start with the real problems your VPs are encountering rather than forcing them through a standardized 12-week program.
• Can challenge them. You want someone willing to say, “Your forecast problem isn't a forecasting problem; it's a management problem,” when appropriate.
• Has a way to measure progress. Establish 2–4 observable outcomes before starting. Executive-coaching firms themselves often emphasize demonstrated impact, senior operating experience, and client references as selection criteria.
• Strong confidentiality boundaries. Your VPs need to be able to discuss the CEO, board, peers, compensation, personnel decisions, etc. without wondering what gets reported back.

I'd run the search like this

1. Define the 2–3 problems each VP needs to solve.

For example:

VP Sales: forecasting, manager effectiveness, enterprise deal strategy, hiring, delegation VP Marketing: pipeline accountability, positioning, Sales alignment, team leadership, strategic prioritization That prevents you from hiring a “great executive coach” who isn't particularly useful to these executives.

2. Get 5–8 candidates.

I'd source them through:

• CEOs/founders in your network
• other CROs/CMOs you respect
• PE/VC operating partners, if applicable
• reputable executive-coaching firms
• specialized revenue-leadership coaching platforms

For example, Exec specifically offers coaching for VPs of Sales/CROs and has coaches with direct revenue/GTM leadership experience.

3. Give each coach the same real problem.

Don't have a generic “chemistry call.” Give them something like:

“Our VP Sales is doing $X in ARR. Forecast accuracy has deteriorated, managers aren't really coaching, and the VP still gets pulled into too many deals. What would you want to understand before coaching them?” The quality of their questions will tell you a lot.

4. Ask for references from comparable executives.

I'd specifically ask:

“Can I speak with two CEOs or executive sponsors whose VP/CRO/CMO you coached?” Then ask those references what actually changed—not whether they “liked” the coach.

5. Start with a 90-day pilot.

Don't sign a year-long engagement initially. Give the coach clear outcomes, e.g.:

• VP spends less time operating at the wrong altitude
• Forecast reliability improves
• Sales/Marketing conflict decreases
• Managers become more accountable
• VP makes faster, higher-quality decisions
• CEO no longer has to be the escalation point

Then reassess after 90 days.

One important distinction

I'd also determine whether you actually need coaching, mentoring, or an operating advisor.

If the VP knows what to do but struggles with delegation, conflict, executive presence, or decision-making → coach.

If they need someone who's “been there” to give them perspective on scaling a revenue organization → mentor.

If the sales/marketing machine itself is broken—territories, funnel architecture, compensation, forecasting, org design, GTM strategy → operating advisor may be more valuable than a coach.

My preferred setup for your situation

If both VPs need development, I'd avoid automatically giving them the same coach. I'd find one strong coaching firm or network, have each VP meet 3 candidates, and let each choose from a vetted shortlist. That preserves individual fit while giving you a consistent standard and procurement process.

If you tell me your company size/revenue, B2B vs. B2C, industry, and what you most want the VPs to improve, I can research and give you a shortlist of 5–10 specific sales/revenue leadership coaches, including why I'd consider each one and what I'd ask them in the first interview.

Finding a top-tier sales leadership coach for your VPs of Sales and Marketing requires looking beyond generic executive coaching . You need practitioners who understand pipeline velocity, go-to-market (GTM) alignment, quota attainment, and the distinct psychology of leading modern revenue teams.

Here is a step-by-step framework to find, vet, and hire the right coach:

1. Define the specific objectives

• Determine whether your VPs need help with strategic scaling (building out enterprise tiers, international expansion), operational execution (forecasting accuracy, CRM discipline, rep accountability), or interpersonal leadership (managing up, cross-functional alignment between sales and marketing, preventing burnout).

1. Look in the right networks and platforms

• Revenue-Specific Advisory Firms: Look at organizations like Pavilion (formerly Revenue Collective), which houses vetted GTM executives and coaching matching.
• Top-Tier Boutiques & Industry Experts: Search for coaches who are former CROs or CMOs of scaling tech/B2B companies rather than theoretical life coaches. Check out platforms like Chief (if your VPs qualify for executive women's networks) or peer-advisory groups like Vistage for leadership development programs.
• LinkedIn & Referrals: Search keywords like "B2B Sales Leadership Coach," "Revenue Executive Coach," or ask fellow founders and portfolio operations partners in your VC/PE network for direct peer recommendations.

1. Vet candidates rigorously

• Ask about their operating background: A good sales leadership coach should have scars from the field. Ask: "What was the largest team you managed, and what was the toughest quota miss you navigated?"
• Inquire about their methodology: Do they use a structured framework (e.g., MEDDPICC-aligned coaching, Challenger sale reinforcement, or specific executive EQ frameworks), or is it purely conversational venting sessions?
• Request a pilot or sample session: Have your VPs do a 30-minute alignment/trial session with the coach. Chemistry is non-negotiable; if your VPs don't respect the coach's operational chops immediately, the coaching will fail.

1. Establish clear accountability metrics

• Ensure the engagement isn't open-ended without guardrails. Set a 3-way alignment meeting (you, the coach, and the VP) to outline 2-3 specific behavioral or performance outcomes for a 90-day sprint (e.g., shortening sales cycles by 15% or improving marketing-to-sales lead handoff efficiency).

If you'd like, tell me:

• What is the industry and size of your company (e.g., early-stage startup, mid-market B2B)?
• Are you looking to fix a specific challenge (like missed forecasts or friction between sales and marketing) or focus on general leadership growth?

I can give you more tailored recommendations on where to look or what interview questions to ask.

Finding a high-impact sales and marketing leadership coach for executives at the VP level requires a different playbook than hiring a standard sales trainer or life coach. VPs don't need tactical "how to cold call" advice; they need strategic sparring partners who understand organizational design, cross-functional alignment (especially between sales and marketing), board-level forecasting, and scaling revenue engines.

A structured, step-by-step framework can help you source, vet, and select the right coach for your executive team.

Step 1: Diagnose the Specific Gap (Sales vs. Marketing vs. Alignment)

Before looking at profiles, clarify what "good" needs to fix. VPs typically struggle in one of three arenas:

• The Builder vs. The Scaler: Do they need help building a pipeline, compensation structure, and attribution model from scratch, or do they need to optimize an existing engine and manage enterprise scale?
• The Cross-Functional Chasm: Is the core issue that your VP of Sales and VP of Marketing are operating in silos and blaming each other for lead quality or conversion rates? If so, they may benefit from a coach who specializes in joint go-to-market (GTM) alignment.
• Executive Presence & Board Pressure: Do they struggle with managing up, defending forecasts to the board, or transitioning from a high-performing "super-rep" to an executive strategist?

Step 2: Define the Ideal Coach Profile

Executive coaches at this tier generally fall into three buckets. Look for someone who matches your company stage:

• Former Operators (Fractional CROs / CMOs): Coaches who have sat in the exact seat, scaled a company through your current revenue milestone (e.g., $10M to $50M ARR), and understand modern revenue architectures. Best for practical execution, GTM strategy, and pipeline metrics.
• Behavioral & Leadership Psychologists: Certified executive coaches (ICF-credentialed, Marshall Goldsmith-trained, etc.) who focus on emotional intelligence, leadership blind spots, communication, and team dynamics. Best for interpersonal friction, ego management, and burnout.
• Cohort-Plus-1:1 Hybrid Programs: Structured organizations like Vistage or specialized revenue leadership groups that combine peer advisory boards with personalized executive coaching. Best for combating isolation at the top.

Step 3: Sourcing Channels

Avoid generic Google searches. Instead, source through trusted channels where executive revenue leaders hang out:

• Peer Networks & Founder Communities: Ask fellow CEOs in your network (via Slack communities like Pavilion, RevGenius, or local EO/YPO chapters) who specifically coached their revenue VPs. Word-of-mouth is the gold standard here.
• GTM Advisory & Boutique Firms: Look at specialized leadership development groups that focus on executive coaching tailored to revenue teams rather than generic corporate coaching.
• Vetted Directories: Organizations like the International Coaching Federation (ICF) credential holder directory allow you to filter by executive coaching specialties.

Step 4: The Vetting & Interview Process

When you bring a prospective coach into an alignment call, test them with real scenarios:

1. Ask for their framework on Sales/Marketing alignment: If they treat sales and marketing as completely separate entities, walk away. A top-tier GTM coach understands that a breakdown between these two functions is usually a symptom of a broken shared definition of revenue velocity.
2. Request a case study: Ask: "Tell me about a VP who was missing their number and struggling with their team. What was the diagnosis, and what did the intervention look like over 90 days?"
3. Check for "pushback" capability: VPs of sales and marketing can be strong-willed, charismatic, and defensive. Watch how the coach handles you in the interview. If they just nod and agree with everything you say, they won't have the backbone to challenge your VPs when they are deflecting responsibility.
4. Establish clear KPIs: While coaching is personal, organizational coaching must tie back to behavior and business outcomes—such as forecast accuracy, retention of key team members, shorter sales cycles, or improved lead-to-opportunity conversion rates. Typical engagements run on a 6-to-12-month cadence with monthly or bi-weekly 1-on-1 sessions.

To help narrow down the search, tell me:

• What is your company's approximate stage or ARR (e.g., early-stage startup vs. mid-market)?
• Is the primary friction internal alignment between sales and marketing or individual leadership performance?

For VPs of Sales and Marketing, I’d look for an executive coach who understands revenue leadership, not a generic “sales coach.” At that level, the biggest gains are usually around strategic judgment, executive presence, cross-functional alignment, talent, forecasting/accountability, and influencing the CEO/board—not just sales techniques.

What I’d look for

• Has actually coached VPs/C-suite leaders. Ask for 3–5 anonymized examples of people at a similar level and what changed as a result.
• Understands the revenue system. Ideally they have substantial experience with sales, marketing, GTM, pricing, pipeline, customer strategy, and the Sales/Marketing relationship.
• Strong coaching credentials. I’d favor an established executive-coaching credential such as ICF/EMCC/AC, while treating credentials as a filter rather than proof of effectiveness. The Association for Coaching, for example, has explicit executive-coach accreditation levels and competency/ethics requirements.
• Business experience, not just coaching experience. For your audience, I'd be particularly interested in someone who has been a CRO, CMO, VP Sales, CEO, or senior operating executive—or who has spent years coaching those people.
• Outcome-oriented. The coach should help define measurable objectives at the beginning and revisit them throughout the engagement. The strongest executive-coaching standards explicitly emphasize business impact and return on engagement.
• Can coach two executives without creating politics. If you're coaching both your VP Sales and VP Marketing, confidentiality and boundaries matter enormously.

I would run the selection like this

1. Define the 2–4 outcomes for each VP.

For example:

VP Sales

• Become a stronger enterprise-level leader
• Improve forecast discipline and operating cadence
• Develop the next layer of sales leadership
• Improve strategic deal/customer involvement

VP Marketing

• Become a stronger commercial partner to Sales
• Sharpen positioning/GTM strategy
• Increase executive influence
• Build a higher-performing marketing leadership team

2. Get 5–8 candidates.

I'd source them through:

• CEOs/CROs/CMOs you respect
• Your board/investors
• Other executives in your network
• Executive-coaching firms
• Professional coaching bodies

I'd actually favor warm referrals from CEOs and CROs over Google-style lists.

3. Interview 3–4 coaches yourself.

Give each the same hypothetical situation:

“My VP Sales is commercially strong but too tactical and doesn't develop her team. My VP Marketing is talented but isn't sufficiently aligned with Sales. How would you approach coaching them?” You're looking for the quality of their questions—not the cleverness of their answer.

4. Have each VP meet the finalist separately.

This is critical. The coach needs to be someone the executive will trust enough to discuss weaknesses, politics, mistakes and ambitions.

5. Ask for references.

Don't just ask, “Were they good?”

Ask:

• “What changed in the executive?”
• “What was the coach particularly good at?”
• “Where was the coach weak?”
• “Would you hire them again?”
• “Did the coach understand the business, or mostly the person?”
• “What happened when the executive resisted the coaching?”

One important distinction

I'd decide whether you want individual executive coaching or revenue-leadership coaching.

If the problem is primarily “these are good executives who need to become exceptional leaders,” I'd choose a superb executive coach.

If the problem is “Sales and Marketing aren't operating as one revenue organization,” I'd consider a coach who can work with both VPs plus you/CEO around the operating system—not simply two separate coaching engagements. Executive coaching is particularly useful when it helps leaders translate development into real-time organizational challenges and sustained behavior change.

A firm such as ccl.org is worth looking at as a benchmark for what a scaled executive-coaching offering looks like; they emphasize coach quality management, supervision, reporting and leadership-development outcomes.

My preferred setup

For two VPs, I'd probably start with a 6-month engagement, roughly:

• 60–90 minute session every 2–3 weeks
• Initial stakeholder/360-style assessment
• Explicit goals agreed among the VP and coach
• Very high confidentiality
• Monthly/quarterly check-in with you focused only on agreed outcomes, never confidential content
• Midpoint assessment
• Clear definition of what “success” looks like at month 6

And I'd avoid coaches who promise to “fix” your VPs. The best coach should make your executives more capable of solving their own problems—not make them dependent on the coach.

If you tell me (a) your company size/stage, (b) whether Sales and Marketing currently report separately, (c) what you think each VP most needs to improve, and (d) your approximate coaching budget, I can also help you build a shortlist of actual coaches/firms and a scorecard for interviewing them.

Don't just ask, “Were they good?”

Ask:

• “What changed in the executive?”
• “What was the coach particularly good at?”
• “Where was the coach weak?”
• “Would you hire them again?”
• “Did the coach understand the business, or mostly the person?”
• “What happened when the executive resisted the coaching?”

One important distinction

I'd decide whether you want individual executive coaching or revenue-leadership coaching.

If the problem is primarily “these are good executives who need to become exceptional leaders,” I'd choose a superb executive coach.

If the problem is “Sales and Marketing aren't operating as one revenue organization,” I'd consider a coach who can work with both VPs plus you/CEO around the operating system—not simply two separate coaching engagements. Executive coaching is particularly useful when it helps leaders translate development into real-time organizational challenges and sustained behavior change.

For VPs of Sales and Marketing, I’d look for an executive leadership coach with real go-to-market experience, not a generic “sales coach.” The distinction matters: your VPs are probably dealing with executive-team dynamics, strategy, talent, forecasting, cross-functional alignment, and organizational leadership—not just sales technique.

Research is broadly supportive of executive coaching, with randomized-trial meta-analyses finding meaningful effects across leadership and personal outcomes.

What I would screen for

• Has coached at the VP/CRO/CMO level. Ask specifically for examples of executives they've coached, not just “20 years of leadership experience.”
• Understands B2B revenue organizations. Ideally they've worked with sales + marketing + customer success/product, and understand pipeline, forecasting, GTM strategy, hiring, compensation, and board/CEO expectations.
• Can coach rather than consult. A great operator isn't automatically a great coach. ICF's standards emphasize listening, curiosity, client-generated insight, and maintaining the coaching role rather than simply telling the executive what to do.
• Comfortable with measurable business outcomes. I'd want goals such as improving forecast accuracy, executive presence, talent retention, delegation, cross-functional alignment, or leadership-team effectiveness—not vague “personal growth.”
• Has references from people at the same level. ICF recommends interviewing multiple coaches and asking for references.
• Strong confidentiality boundaries. This is particularly important if you are paying for the coaching but the VP is the client.

I'd actually run a mini-RFP

Give 4–5 coaches the same brief:

“We have VPs leading Sales and Marketing. We're looking to strengthen executive leadership, cross-functional alignment, talent development, and business performance. The CEO wants visibility into agreed-upon development objectives, but individual coaching conversations must remain confidential.” Then ask each coach:

1. Who are 3–5 executives you've coached recently who resemble these VPs?
2. What business problems did they bring you?
3. What changed as a result?
4. How do you establish goals and measure progress?
5. What would you do differently coaching a VP Sales versus a VP Marketing?
6. How do you handle a situation where the executive's stated problem isn't the real problem?
7. How do you work with the CEO/CHRO while protecting the executive's confidentiality?
8. Can I speak with two former clients?
9. What happens if the executive and coach aren't a good fit?
10. What would you want to learn about our company before agreeing to coach them?

That last question is surprisingly revealing.

One important decision: one coach or two?

I wouldn't automatically give both VPs the same coach.

One coach for both makes sense if you're trying to create a common leadership language or improve Sales–Marketing collaboration. The coach gets useful organizational context.

Separate coaches may be better if the VPs have substantially different development needs—or if you want each person to feel completely unconstrained in the coaching relationship.

A good compromise is to have one coaching firm/program with two individual coaches, plus a common framework and occasional organizational-level check-ins.

Where I'd start looking

The coachingfederation.org is a useful starting point. I would particularly filter for PCC or MCC credentials and executive coaching, then independently verify the person's actual GTM/executive experience. ICF's credentialing process evaluates coaches against defined coaching competencies rather than simply accepting a coach's own claims about expertise.

I'd also use CEO/board/CHRO referrals. For this level of executive, a referral from another CEO who has actually used the coach is often more valuable than a polished coaching website.

My ideal profile

If I were hiring for your situation, my target would be:

Former senior operator + professionally trained executive coach + extensive VP/C-suite coaching experience + B2B GTM expertise + strong references.

I'd favor that combination over someone who is an outstanding salesperson but has little evidence of coaching executives.

If you tell me your company size, B2B/B2C, approximate revenue, industry, and whether the primary goal is developing the VPs individually or improving Sales–Marketing performance, I can also help you build a shortlist of actual coaches/firms and a scorecard for choosing among them.

Finding a high-impact sales leadership coach for your VPs of Sales and Marketing requires a targeted approach, as executive coaching at this level blends strategic revenue growth, team alignment, and leadership development.

Here is a step-by-step framework to find, vet, and select the right coach:

To help narrow down the ideal profile, could you share:

• What is your company's industry and stage (e.g., Series B SaaS, mid-market enterprise)?
• Are you looking for separate coaches for each VP or a single coach who can align both functions?

Yes. For VPs of Sales and Marketing, I’d avoid generic “executive coaches” and look for someone who understands the intersection of revenue strategy, leadership, GTM, and executive-team dynamics.

A useful way to approach it:

1. Define what you actually want to change

Before interviewing coaches, give each VP a short development brief. For example:

• VP Sales: forecasting discipline, hiring/managing directors, executive presence, coaching managers, strategic account leadership, board communication.
• VP Marketing: GTM alignment with Sales, positioning, demand generation, managing a larger team, prioritization, executive influence.
• Both: cross-functional conflict, decision-making, accountability, delegation, leading through growth/change.

The best coaching engagements connect behavioral change to business outcomes—not simply “become a better leader.”

2. Look for an operator, not just a credential

For your particular audience, I'd weight these heavily:

Credentials such as ICF certification are useful, but they shouldn't outrank experience and fit. One executive-coaching firm, for example, uses prior senior business leadership, formal coach training, external coaching experience, and judgment/self-awareness as selection criteria.

3. Interview 5–8 coaches, then give 2–3 a chemistry session

I'd ask every candidate:

1. “Tell me about three VPs of Sales you've coached. What changed?”
2. “What did you actually do when the executive wasn't changing?”
3. “How do you distinguish a coaching problem from an organizational/structural problem?”
4. “How would you coach a VP Sales and VP Marketing who aren't aligned?”
5. “What will you measure at the beginning and end?”
6. “What do you need from me as CEO?”
7. “What would cause you to tell me that coaching isn't the right intervention?”

That last question is particularly revealing. A good coach shouldn't try to turn every organizational problem into a coaching engagement.

4. Consider two coaches rather than one

If these are genuinely senior VPs, I'd generally prefer:

One coach per executive + occasional joint/team coaching

rather than forcing both executives into the same coaching relationship.

They may have completely different developmental needs, while the shared sessions can focus on things like Sales/Marketing alignment, strategic decision-making, and executive-team effectiveness.

There are also platforms with networks specifically covering VPs of Sales/CROs and revenue leadership, such as exec.com, which can be useful if you want to compare multiple coaches rather than finding a single independent coach.

For a more hands-on sales-specific approach, salesxceleration.com uses former VP/C-level sales executives as coaches.

5. Run a 90-day pilot

I wouldn't sign a year-long coaching contract initially.

I'd do:

Weeks 1–2: stakeholder interviews + baseline Weeks 3–12: biweekly 1:1 coaching Day 30: behavioral goals reviewed Day 60: progress check Day 90: CEO + executive + coach assessment

Define 2–4 observable outcomes per VP. For example:

“By day 90, the VP Sales is consistently delegating forecast inspection to directors, has improved forecast confidence, and is spending materially more time on strategic accounts and leadership development.” That makes the engagement much easier to evaluate than “the VP feels more confident.”

Where I'd start

If you tell me (1) your company size/revenue, (2) B2B or B2C, (3) industry, (4) whether these VPs are first-time or experienced VPs, and (5) roughly what you'd like to spend per executive, I can research and give you a shortlist of 5–10 actual coaches/firms, including their backgrounds, specialties, pricing where available, and which I'd interview first.

To find a good sales leadership coach for your VPs of Sales and Marketing, look for professionals with proven executive-level operating experience, strong peer recommendations, and a methodology tailored to high-growth alignment.

Watch this video from Pivotal Advisors to understand how effective coaching builds critical sales and leadership capabilities:

5:26 How Great Sales Leaders Develop Their People 5 months ago YouTube · Pivotal Advisors, LLC

Steps to Find and Vet a Sales Leadership Coach

- Identify whether your VPs need help with **strategy, team accountability, cross-departmental alignment** between sales and marketing, or **execution habits**. [1][2]

- Use professional networks and peer communities like Pavilion to source recommendations for executive coaches who specialize specifically in revenue leadership. [1]

- Look into dedicated B2B advisory and coaching organizations such as Pivotal Advisors or industry experts like Mike Weinberg's Leadership Cohort for structured executive programs. [1]

- Verify that the coach has actual, recent experience as a **former VP of Sales or Chief Revenue Officer (CRO)** rather than just a theoretical trainer. [1]

- Ask candidates about their **frameworks for accountability** , how they handle the unique tension between sales and marketing, and request client references from current executive VPs. [1]

If you'd like, let me know:

• Are your VPs struggling more with team execution or strategic alignment between sales and marketing?
• Are you looking for a 1:1 private coach or a group cohort program?

I can give you more targeted recommendations based on your preferences.

Finding a strong sales leadership coach for your VPs of Sales and Marketing is less about finding a “sales trainer” and more about finding someone who can help senior leaders improve judgment, operating cadence, executive presence, cross-functional alignment, and revenue execution.

Here is a practical approach:

1. Define the outcome before you search

Start by identifying what you want the coach to change. Common goals for VP-level leaders:

• Build a more predictable pipeline and forecast
• Improve sales-manager coaching skills
• Create stronger Sales/Marketing alignment
• Improve executive communication with the CEO/board
• Scale from founder-led or hero-led selling to a repeatable system
• Strengthen hiring, talent evaluation, and accountability
• Improve strategic planning and GTM execution

A coach who specializes in first-time VP Sales leaders may not be the right fit for an experienced CRO managing a $100M+ revenue organization.

2. Look for operator experience, not just coaching credentials

For VPs, prioritize coaches who have actually:

• Been a VP Sales, CRO, VP Marketing, or revenue executive
• Built teams through growth stages similar to yours
• Managed the Sales/Marketing relationship themselves
• Owned a number or revenue target
• Experienced the problems your leaders face

There are firms and advisors that specifically position themselves around coaching revenue executives, including former sales executives and revenue leaders. Examples include Sales Xceleration, which uses former sales executives as advisors, and REACH•ABLE, which focuses on coaching revenue leaders with operator backgrounds.

3. Interview 5–8 candidates with these questions

Ask:

Experience

• “What type of sales organizations have you personally led?”
• “What was the largest team and revenue responsibility you owned?”
• “What industries and sales motions do you know best?”

Coaching approach

• “How do you determine whether a VP’s issue is skill, strategy, mindset, or organizational design?”
• “What does a typical 90-day coaching engagement look like?”
• “How do you measure improvement?”

Business impact

• “Tell me about a VP you coached who changed materially. What changed?”
• “What metrics moved afterward?”
• “How do you avoid becoming just another consultant giving advice?”

Fit

• “How do you handle situations where the CEO, VP Sales, and VP Marketing disagree?”
• “How do you coach executives who are defensive or already successful?”

4. Avoid these warning signs

Be cautious if a coach:

• Only teaches sales methodologies but has never led sales
• Focuses heavily on scripts and tactics for VP-level leaders
• Cannot explain how they diagnose leadership problems
• Promises revenue results they cannot control
• Has no experience with your sales model (enterprise, SMB, PLG, channel, etc.)

5. Consider the engagement model

Common formats:

• 1:1 executive coaching: Best for a VP who needs leadership growth, confidence, decision-making, or strategic thinking.
• Revenue leadership coaching: Best when Sales and Marketing leaders need to operate as a team.
• Embedded advisory: Best when you need someone to help redesign processes, cadence, forecasting, and org structure while coaching leaders.
• Executive offsites + ongoing coaching: Good for leadership teams going through growth transitions.

Some providers combine coaching with operating-system work, such as forecast discipline, pipeline inspection, and leadership cadence.

6. Use your network strategically

The best referrals often come from:

• CEOs who have scaled a similar company
• Board members or investors
• Other CROs/CMOs in your industry
• Executive recruiters who place revenue leaders
• Former VPs who have worked with excellent coaches

Ask specifically: “Who helped you become a better executive leader?” rather than: “Do you know a sales coach?”

7. Run a paid trial before committing

A good structure:

• 30–60 day diagnostic phase
• Interviews with the VP, CEO, and key stakeholders
• Review of pipeline, org structure, KPIs, and operating rhythms
• Clear coaching goals and success measures
• Decision to extend

A strong coach should be willing to define what success looks like before a long engagement.

If you share your company stage (startup/growth/enterprise), sales motion (enterprise SaaS, SMB, channel, etc.), and the specific challenges your VPs are facing, I can suggest the type of coach profile that is most likely to work.

To find a great sales leadership coach for your VPs, you must look for an executive coach with direct, historical experience running a dual sales-and-marketing engine . Because your VPs manage both top-of-funnel generation and bottom-of-funnel closing, a generic sales trainer who only focuses on closing deals will fail to address their cross-functional leadership challenges.

1. Where to Look for Elite Coaches

• Retired or fractional Chief Revenue Officers (CROs): Seek out former VPs or CROs who have successfully scaled similar organizations and transitioned into coaching. They offer firsthand strategic advice and high accountability.
• Executive Search and Recruiting Firms: Top firms often maintain private, vetted networks of elite enterprise mentors and leadership coaches.
• Niche Venture Capital / Private Equity Portfolios: If you are backed by investors, leverage your VC or PE operating partners. They frequently keep lists of tested coaches specializing in scaling leadership.
• Specialized B2B Sales Networks: Explore trusted enterprise platforms or look into top-tier executive programs like the Mike Weinberg Sales Leadership Coaching Cohort.

2. Crucial Qualities to Vet

When interviewing potential coaches, use a strict checklist to verify they can coach a modern VP:

• Cross-Functional Alignment Mastery: The coach must understand how to align sales pipelines with marketing attribution, rather than just treating them as separate departments.
• "Coach the Coach" Capabilities: Your VPs do not need help closing deals. They need help building a structured coaching cadence, developing pipeline tracking systems, and driving accountability down to their managers.
• SaaS or Industry-Specific Context: Ensure the coach knows your specific business model (e.g., PLG, enterprise outbound, or channel sales) so they don't give outdated advice.

3. Interview Questions to Ask Candidates

Screen potential coaches with these direct, behavioral questions to test their business acumen:

1. "Can you walk me through how you helped a previous executive navigate alignment issues or tension between marketing lead generation and sales execution?"

2. "What specific frameworks or data tools do you use to help a VP transition from being a tactical operator to a legacy strategic leader?"

3. "How do you measure the ROI of your engagement? Can you share the metrics or revenue growth achieved by the last three VPs you coached?"

4. Structuring the Engagement

To guarantee success, ensure the coaching contract includes three distinct phases:

• Phase 1: Deep Assessment. The coach should start by auditing your current pipeline metrics, sitting in on your VPs' team meetings, and collecting 360-degree feedback from their direct reports.
• Phase 2: Tailored 1:1 Cadence. Sessions should occur every two weeks, blending high-level strategy with strict execution accountability.
• Phase 3: Stakeholder Alignment. The coach should meet with you (the CEO/Founder) quarterly to review progress, ensuring the leadership development matches your company's broader revenue targets.

To help point you in the right direction, what are the biggest challenges your VPs are facing right now? (e.g., hitting revenue quotas , managing a growing team , or fixing sales-marketing alignment?)