Total Search Time: 4 months

Lead Source: Executive recruiter relationship 

Bespoke Partners. The recruiter had reached out previously about other opportunities that didn't work out timing-wise, but maintained the relationship by saying, "If something else comes up, we'll come back to you." The key was being responsive and building a friendly dialogue rather than purely transactional interactions.

Job Landed Time: 6-8 weeks from first contact to offer

Time/Personal Management

• Prioritized being "very responsive" to recruiters and maintaining friendly dialogue

• Practiced answers by recording himself on Zoom calls

• Maintained mental health through positive focus during early rejections

• Focused on learning emerging topics like AI best practices during downtime

Networking & Tools

• Signed up for Above Board (True Search's platform for marketing leaders)

• Used ChatGPT and Gemini extensively to research companies and prepare interview questions

• Leveraged the CMO Huddles Huddle Buddies playbook for preparation strategies

Anticipate Objectives

• Identified and consistently addressed two main objections: lack of industry experience and ability to operate in a smaller company environment

• Positioned product background as transferable to new industry

• Emphasized scale experience ($200M to $500M revenue growth) as key differentiator

Interview Process:

First Interview Strategy

"The single best thing that I did early on was... we spent probably 70% of the time with me asking questions about their space and the company, everything else. And he loved that."

Key tactics:

• Dropped off a call when the interviewer was 15 minutes late, sending a message about valuing time

• Came prepared with extensive questions researched via AI tools and recruiter insights

• Asked recruiter for background on interviewers to tailor approach

• Focused on understanding the business rather than selling himself initially

Full Process Overview:

1. Initial screening with head of marketing/product (twice - second meeting requested to cover background after asking too many questions in first)

2. HR interview for culture fit assessment

3. CEO interview

4. Last-minute in-person panel (Boston) - "Can you come tomorrow?" test

   • Met with finance, legal, and other functions (notably not sales until very end)

   • Received panel list morning of interview (6 people vs. expected 2-3)

5. 30-60-90 day plan (requested after another candidate proactively submitted one)

6. Final interviews with head of sales and CEO

Interview Preparation Insights:

• Researched CEO through YouTube videos and presentations

• Discovered company's M&A strategy (9 acquisitions in 10 years) and prepared for acquisition-related questions

• Treated every conversation as a late-stage interview, including informal check-ins

The 30-60-90 Day Plan Differentiator:

"The CEO told me afterwards he liked that I didn't have a prescribed playbook that I would walk in because he was worried I didn't know enough about the business to even go there."

Winning approach:

• Focused on hypotheses rather than prescribed actions

• Linked everything back to business understanding (mid-market expansion, global growth in Japan/Germany)

• Oriented around "needle movers" like digital marketing efficiency and scale

• Avoided tactical, standard playbook approach that other candidates used

Competitive Dynamics:

Pursued two opportunities simultaneously. The competing opportunity helped create urgency and faster decision-making from the winning company.

Negotiation Process:

Limited details provided, but having competing late-stage opportunities accelerated the offer process and likely strengthened negotiating position.

Critical Mistakes to Avoid:

1. No "informal" meetings exist - "There is no such thing as an informal meeting in the job search."

2. Always be presentation-ready - Lost another opportunity by not preparing adequately for a last-minute presentation request.

3. Stay connected with recruiters - Admitted to making the mistake of not maintaining recruiter relationships while employed/

Mental Health Management:

"It's so important around the mental health side, because early on there were like 3 or 4 opportunities that came up fast... and every one of them just disappeared... and that messed with my head."

Coping strategies:

• Used rejection periods to focus on learning (AI, best practices)

• Maintained belief in qualifications despite early ghosting experiences

• Leveraged support system and professional development during downtime

Strategic Insights:

• PE vs. VC dynamics matter - Understanding where PE firm is in lifecycle (newly acquired vs. 4+ years owned) is crucial

• Industry experience isn't everything - Scale experience and ability to ask smart questions can overcome sector knowledge gaps

• Questions > Answers - Demonstrating curiosity and business acumen through questioning impressed more than having all the answers

• Consistency in messaging - Repeatedly addressing known objections throughout process builds confidence

Key Success Factors:

1. Preparation depth - Extensive research using AI tools, recruiter insights, and CEO content

2. Strategic patience - Willing to walk away from opportunities that didn't respect time/priorities

3. Authentic engagement - Built genuine relationships rather than transactional interactions

4. Business focus - Oriented everything around the company's strategic priorities rather than personal capabilities

5. Adaptability - Showed willingness to learn rather than impose predetermined solutions

This case illustrates how thorough preparation, strategic relationship building, and business-first thinking can expedite a senior executive search process, even when transitioning into a new industry.