Build a C-suite for Scale: When to Hire CFO, Head of Strategy and Growth During a Reboot

Hook: You can’t scale what you can’t staff — and timing kills

Pain point: You’re planning a major reboot or growth push but you don’t know which executives to hire, when to hire them, or what the hires should deliver first. Hire too early and you bleed equity and payroll; hire too late and you miss revenue, run out of runway, or lose strategic control.

Executive summary — the answer up front

Inspired by Vice Media’s early-2026 reboot hires (they brought on a seasoned CFO and an EVP of Strategy as they pivoted from agency/production-for-hire back to being a content studio), this article gives you a practical, time-stamped hiring timeline and role checklists for: CFO hiring, Head of Strategy, and Head of Growth. Use the timeline to map hires to cash runway, product maturity, and monetization complexity.

Fast takeaway: if you’re moving from survival & product validation into a deliberate growth chapter, hire in this order and at these signals — first financial control (CFO or fractional CFO), then strategic architecture (Head of Strategy), and then the engine to scale revenue (Head of Growth). Add Ops/COO later to operationalize scale.

Why Vice Media’s reboot is a useful template for small companies in 2026

In late 2025 and early 2026, Vice Media moved through a bankruptcy-to-reboot cycle and publicly expanded its C-suite, hiring Joe Friedman as CFO and bringing on Devak Shah in a strategic growth role as part of a broader repositioning toward studio and IP ownership. That sequence — stabilize finances, reset strategy, then accelerate growth execution — is the playbook smaller firms should copy on a timeline that fits their runway and stage.

“Joe Friedman will join Vice Media as CFO while Devak Shah has been hired as evp of strategy.” — The Hollywood Reporter, Jan 2026

2026 context you must build for

• Fractional C-suite mainstreamed: late‑2024 through 2025 venture cooling means boards demand path-to-profitability or clear M&A paths.
• AI-enabled growth: cookieless adtech, first-party data strategies, and regional privacy laws (post-2023/2024 rollouts and new state laws through 2025) require coordinated legal, product and growth responses.
• M&A & strategic partnerships: strategic hires are often brought in to package assets (content, IP, tech) for partnership or sale.
• Fractional C-suite mainstreamed: fractional CFOs and Heads of Growth are now credible stop-gaps through marketplaces matured in 2024–2026.
• AI-enabled growth: 2025–2026 saw broad adoption of AI for CRO, personalization, and GTM automation — your hires must be comfortable integrating AI tooling and vendor partnerships.

Hiring timeline: phases and signals

This timeline maps the four phases of a reboot-to-scale journey to hiring milestones. Adjust windows for your runway and ARR.

Phase 0 — Reboot Week 0–3: Stabilize (Founders + contractors)

• Who leads: Founders, interim CFO (fractional), freelance legal counsel
• Signals: immediate cash scarcity, urgent vendor negotiations, restructuring needs
• Priority hires: fractional CFO or turnaround FP&A; external legal for bankruptcy/contract work

Phase 1 — Stabilize & Rechart (Months 0–6)

• Who leads: permanent CFO or senior finance hire (if runway allows), Head of Strategy (senior, could be interim)
• Signals for hiring CFO: complex revenue streams, fundraising on the table, GAAP accounting needs, or active M&A/partner negotiations
• Signals for Head of Strategy: pivot or business-model change; need to repackage offerings; new IP strategy
• Outcomes expected: runway extended, new 12–24 month plan, prioritized product/monetization roadmap

Phase 2 — Execute & Scale (Months 6–18)

• Who leads: Head of Growth (performance-driven hire), marketing ops, revenue ops
• Signals for hiring Head of Growth: validated monetization, sustainable unit economics (or clear path), need to scale CAC-efficient channels
• Outcomes expected: repeatable acquisition funnels, revenue growth, foundational analytics stack

Phase 3 — Run the Machine (Months 18–36)

• Who leads: COO or President to integrate functions, expanded finance team, product leadership
• Signals: >$5–10M ARR growth, multiple business lines, need for centralized ops and governance
• Outcomes expected: sustainable margins, scalable org design, maturity-ready for IPO/strategic sale

Who to hire, when — role-by-role playbook

The CFO: When to hire, checklist, and 30–90 day plan

Why hire: The CFO turns cash chaos into decision-grade numbers. In reboots, CFOs negotiate with creditors, structure deals, and design financial models that support strategy.

Signals you need a CFO now

• Multiple revenue streams and complex recognition (subscriptions, ad rev, production contracts)
• Fundraising, debt refinancing, or active M&A conversations
• Cash flow problems, inconsistent forecasting, or audit needs
• You require investor credibility — a seasoned CFO increases valuation defensibility

CFO hiring checklist (must-have capabilities)

• Financial controls & governance: implement month-end close, forecasting cadence, cash-flow modeling
• Capital strategy: fundraising, refinancing, debt negotiations
• Revenue ops: revenue recognition, pricing, contract structuring
• Stakeholder management: board reporting and investor relations
• Operational partnering: work with Head of Strategy on monetization scenarios and with Head of Growth on LTV/CAC models

CFO 30–60–90 day plan

1. Days 0–30: Audit cash, bank covenants, liabilities, revenue contracts. Deliver a 13‑week cash plan and a prioritized risk register.
2. Days 31–60: Implement standardized month-close and basic FP&A model. Rebuild budgets and set new KPIs (gross margin, CAC payback, contribution margin by product).
3. Days 61–90: Present a 12–24 month capital plan tied to strategic milestones; support fundraising or strategic sale preparation.

Head of Strategy: purpose, checklist, and hiring signals

Why hire: The Head of Strategy reframes the business: reposition, productize, or design M&A/partnership blueprints. Vice’s EVP of Strategy was hired to make the jump from production services to a studio model — the exact strategic pivot many small firms face when IP and scalable product opportunities surface.

Signals you need a Head of Strategy

• You’re redefining product-market fit or launching a new monetization model
• You’re packaging IP for partnerships, licensing, or sale
• Board or CEO want a coherent 2–3 year plan with strategic milestones

Head of Strategy hiring checklist

• Market architecture: competitor maps, TAM/SAM/SOM, pricing experiments
• Portfolio strategy: prioritize products, platforms, partnerships
• Commercial models: subscription vs ad vs services transition playbooks
• M&A readiness: asset hygiene, contract standardization, IP packaging
• Cross-functional influence: collaborate with finance and growth to tie ops to strategy

Head of Strategy 30–60–90 day plan

1. Days 0–30: Run a rapid strategic audit: revenue by channel, customer cohorts, unit economics, and competitive positioning.
2. Days 31–60: Produce a one-page strategic north star and a 9–12 month roadmap with measurable checkpoints.
3. Days 61–90: Launch 2–3 prioritized pilots (pricing, product bundles, partnership plays) with clear metrics and escalation rules.

Head of Growth: when to hire and what success looks like

Why hire: You need someone to convert the strategic plan into repeatable revenue channels and optimized funnels. The Head of Growth is the engine operator.

Signals you need a Head of Growth

• Product-market fit validated (consistent conversion rates and positive LTV/CAC trends)
• Repeatable sales processes are possible (self-serve or scaled sales)
• Enough data to run statistically significant experiments

Head of Growth hiring checklist

• Analytics & experimentation: A/B testing, cohort analysis, attribution modeling
• Channel ownership: paid acquisition, content funnels, partnerships, SEO
• Sales enablement: onboarding flows, funnel optimization, lifecycle campaigns
• Tech stack: CDP/CRM, experimentation, analytics, marketing automation
• Privacy & compliance: consented first-party data flows

Head of Growth 30–60–90 day plan

1. Days 0–30: Baseline funnels and key conversion steps; identify 3 highest-impact experiments.
2. Days 31–60: Deploy experiments, set up attribution, and remove tech blockers; deliver an acquisition roadmap.
3. Days 61–90: Scale validated channels, optimize CAC payback, and handoffs to ops/sales for ramp.

Organizational design: reporting lines and collaboration patterns

Design the org so each executive can do what they do best without overlapping accountability. Typical structure during a reboot-to-scale might look like:

• CEO sits above strategy and GTM.
• CFO reports to CEO and partners with Head of Strategy on monetization scenarios and with Head of Growth on unit economics.
• Head of Strategy reports to CEO and works cross-functionally with Product and Legal.
• Head of Growth reports to CEO (or CRO) and owns acquisition, activation and early retention.

Keep roles outcome-focused: finance owns cash and governance, strategy owns north-star and portfolio choices, growth owns revenue engine. Avoid making strategy a “project management” function — it should be the measurable architect of future revenue.

Practical interview scorecards — what to test

For each senior hire, use a scorecard that weights outcomes over CV polish. Below are 3 condensed scorecards you can paste into an interview guide.

CFO scorecard (10 points each area)

• Cash & forecasting track record — quantitative examples (past runway extension, models)
• Capital & transaction experience — led raises, refinancings, M&A diligence
• Operational finance — implemented modern FP&A & reporting systems
• Leadership & stakeholder management — board, investors, legal
• Fit for stage & industry — media/content/tech specifics

Head of Strategy scorecard

• Strategic clarity — can they present a 12‑month plan with measurable milestones?
• Commercial creativity — evidence of new monetization models or partnerships
• Operational delivery — turned strategy into pilots and scaled them
• Cross-functional influence — credibility with product, legal, and finance
• Domain expertise — deep knowledge of your sector (e.g., content/IP, SaaS)

Head of Growth scorecard

• Data-driven test & learn history — examples with lift and statistical validity
• Channel mastery — paid, organic, partnerships, SEO
• Tech stack fluency — CDP, CRM, analytics, automation
• Execution speed — how they prioritize and kill failing experiments
• Retention & unit economics focus — LTV, CAC, churn reduction tactics

Compensation and hiring models in 2026 (practical ranges & alternatives)

Salary and equity will vary by geography, company size, and cash position. Use these as starting guidelines — always benchmark with recent offers and advisors.

• CFO: Startup / small company: base $150–300k, total comp with bonus $200–450k; equity 0.5–3% depending on stage. Fractional CFOs: $2k–10k/week depending on scope.
• Head of Strategy: base $140–260k; equity 0.3–1.5% (higher if strategic M&A expected).
• Head of Growth: base $120–240k; equity 0.5–2%; strong performance bonuses tied to ARR or CAC targets.

If runway is short, use high-caliber fractional or interim hires with strict KPIs and changeover clauses. In 2026 these fractional markets are robust and expected by VCs.

Legal basics & monetization hygiene every hire must support

Executives must understand legal and monetization fundamentals. Use this checklist when hiring and onboarding them.

• Corporate form & tax: ensure the entity structure supports equity grants, raises, and potential exits.
• Revenue contracts: standardize client contracts, define IP ownership, revise R&D, and royalty terms.
• Data & privacy compliance: implement consented first-party data flows; confirm CCPA/CPRA/GDPR compliance and prepare for new state laws and EU carve-outs through 2026.
• IP protection: register key IP, document creator agreements, and create licensing playbooks.
• M&A and diligence readiness: maintain clean cap table, audited financials, and contract repository.

Case study: Applying the template to a small media startup

Scenario: You run a niche media startup with $1.2M ARR that's mostly production services but you own a growing content IP with subscription potential. You have 12 months of runway and an interest from strategic partners.

1. Weeks 0–6: Bring in a fractional CFO. Deliver a 13-week cash plan and negotiate vendor terms.
2. Months 2–6: Hire Head of Strategy (senior, part-time if necessary). Produce a strategy to spin IP into a subscription product and a licensing pilot for studios.
3. Months 6–12: After pilots show positive unit economics, hire Head of Growth to scale subscriptions and distribution partnerships. CFO transitions to full-time as revenue complexity increases.
4. Months 12–24: Hire a COO if operations become a bottleneck; prepare financials for strategic partnership or sale.

This mirrors Vice’s approach at a smaller scale: stabilize finance, articulate a studio/IP strategy, then staff the growth engine to commercialize that strategy.

Red flags — when NOT to hire

• Hiring an expensive executive without KPIs or runway to act on them.
• Replacing execution gaps with strategy hires without fixing product or unit economics first.
• Overlapping mandates — two leaders owning the same KPI without clear escalation.

Final checklist before you commit to an executive hire

1. Define 90‑day deliverables and 12‑month outcomes tied to cash and revenue.
2. Set acceptance criteria: what success looks like and how you’ll measure it.
3. Choose the hiring model: full-time, fractional, or interim-to-perm with milestones.
4. Align compensation to outcomes: bonus, equity vesting tied to milestones, and change provisions.
5. Plan for handoffs and cross-functional reporting to avoid duplication and misalignment.

Actionable takeaways — what to do this week

• Run a quick signals audit: are revenue streams complex, is fundraising imminent, is product monetization validated?
• If you have complex contracts or fundraising coming, shortlist a fractional CFO this week and set a 30‑day audit deliverable.
• If you’re pivoting business model or packaging IP, draft a one-page strategy brief and start conversations with Head of Strategy candidates.
• If you have validated unit economics, begin a search for a Head of Growth with a testable 90‑day plan.

Why this sequence works

Finance creates the runway; strategy creates the path; growth executes the scale. Vice Media’s early hires during its 2025–2026 reboot followed the same structure: stabilize finances, redesign the business model toward owned IP and studio economics, then staff the growth engine. For small companies, replicating that sequence — with fractional options where needed — de-risks the reboot and increases odds of hitting sustainable scale.

Closing — next steps and CTA

If you’re planning a reboot this quarter, don’t let politics or vanity hires slow you down. Use the timeline and role checklists above to map exactly who you need and when. Want the editable 30–60–90 templates, scorecards, and a hiring timeline spreadsheet customized for your runway and ARR? Click to download the free toolkit or schedule a 30‑minute advisory review with our fractional C-suite network (fractional options available for immediate placement).

Start by running the 7‑point signals audit this week — and pick the first hire you can afford who will deliver measurable outcomes within 90 days.

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