4 builders who never spoke to each other

Make the first marketing hire a doer, not a strategist

Open with a director level person, or a fractional director rather than a fractional chief, because that level still balances planning against doing the work personally, while a leader who cannot convert strategy into specific tasks leaves the team stalled once the obvious tactics run out. Avoid brand and communications specialists at this stage, and hire a single-tactic specialist only when you already know that tactic is right, since someone paid to do it will never tell you it is the wrong thing.

The method

1. 01

   Do not open with a CMO or VP hire: a leader who cannot convert strategy into specific work leaves the team stalled once its known tactics are exhausted.

2. 02

   Make your first marketing hire a director-level person - a veteran manager or rising VP also works - because that level still balances long-term planning against doing the work personally.

3. 03

   Hire a fractional marketing director, not a fractional CMO. Most small companies need someone with five to seven years running one function who will do the tactical work, not someone setting annual strategy in meetings.

4. 04

   Avoid brand, communications and tradeshow-oriented marketers for the first hire regardless of seniority; awareness work only pays off once you already have a customer base.

5. 05

   Only hire a single-tactic specialist if you already have a solid reason to pursue that tactic and enough expertise to direct them, because someone paid to do X will never tell you X is the wrong thing to do.

What it returned

• $100

  A startup with a CMO, a marketing team of demand-gen, operations and events specialists, and over $100 million raised was completely stuck because nobody bridged strategy and tactics.

• 1

  He states directors typically take 1-3 months to hire, VPs 3-6 months and CMOs 6 or more.

• Natividad suggests finding them on LinkedIn among senior managers and directors, often product marketers

• He rates the value a traditional marketer adds as a first hire at an early-stage software startup as close to zero.

Sources

• The roadmap to Product/Market Fit (PMF)… maybeJason Cohen · longform.asmartbear.com · 5. Focus more on marketing and sales, less on product. · 2023-12-24
• Amanda Natividad — Mastering Content Creation and Audience Engagement – The Bootstrapped FounderAmanda Natividad · thebootstrappedfounder.com · 2023-12-06
• Bugfender: Scaling an Internal Remote Logger to €9,000/MonthJordi Giménez · failory.com · If you had the chance to do things differently, what would you change? · undated
• Learn, build, judge, ship: What to look for in your first (AI) marketerGreg Kogan · gkogan.co · 2025-05-31
• Choosing Your First Marketing HireGreg Kogan · gkogan.co · Seniority and the Strategy-Tactics Spectrum · 2018-08-30
• Should You Hire a Freelancer or a Consultant?Greg Kogan · gkogan.co · 2015-11-18