Chief of Staff, Leading Organizational Growth

As a strategic partner to the CEO, I operate at the intersection of strategy, people, and performance, and enable our leaders to operate at their best through coaching, systems, and culture.

I serve as a force multiplier on strategic execution, leadership development, organizational clarity, cross-functional alignment, and team development.

Purpose

Increase the velocity and clarity of executive leadership by embedding systems that support strategic execution, leadership growth, and cross-functional alignment. I help the CEO and the broader org spend more time on what matters most.

Key Responsibilities

CEO Enablement

• Serve as a thought partner to the CEO on strategic decisions and org priorities
• Anticipate and reduce CEO cognitive and emotional load
• Translate CEO vision into actionable roadmaps with clear ownership
• Design and manage decision-making frameworks that reduce leadership bottlenecks

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Leadership Development & Team Coaching

• Coach emerging and senior leaders and act as a multiplier for team capacity
• Architect executive off-sites, 360 feedback loops, and leadership retros
• Normalize growth conversations, accountability, and strategic reflection

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Org & Strategy Alignment

• Drive execution of cross-functional strategic initiatives
• Lead quarterly/annual planning processes and cadence reviews
• Identify performance gaps across teams and org design
• Track and report on OKRs for the executive team

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Success Metrics

• CEO Strategic Time +30%
• Leadership Alignment Scores +15%
• Team Health Scores >85% organization-wide
• Cross-functional Initiative Completion Rate: >90% on-time delivery
• Retention and promotion rates among emerging leaders: +15%

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Example Week

• CEO enablement & syncs (4–6 hours)
• Leadership development efforts (14–18)
• Strategic project execution (10–12)
• Org alignment & systems work (6–8)
• Async comms, reporting, and triage (3–4)

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Example OKRs / Rocks

Scale CEO’s Strategic Capacity

1. Free up 30% of CEO’s time by delegating key projects + designing support systems
2. Run 3 executive feedback loops with actionable growth plans
3. Implement weekly founder–CoS sync to proactively surface blind spots and strategic decisions

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Increase Leadership Team Effectiveness

1. Move alignment score from 6.5 → 8.0 (via diagnostic & behavioral shifts)
2. Launch quarterly leadership development intensives; participation >90%
3. Operationalize 1:1s, retros, and QBRs across all exec pods

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Build scalable systems for people growth

1. Pilot coaching with top 10% of managers; measure behavioral delta
2. Embed growth prompts into 100% of people systems
3. Team health check scores >80% in all departments

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Our First 90 Days

Week 1–2: Orientation & Immersion

Goals:

• Understand company vision, strategy, and current team dynamics
• Establish a working rhythm with the CEO

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Activities:

• 1:1 deep dives with CEO, exec team, and key cross-functional leaders
• Shadow all exec meetings (leadership syncs, board prep, offsites)
• Review OKRs, company values, culture docs, and team performance reviews
• Plug into company workstreams: e.g. Notion, Slack, Asana, comms, analytics tools, etc.

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Deliverables:

• “Top 10 Leverage Points” memo with recommended interventions
• Draft of working agreement with CEO: expectations, cadence, preferences

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Week 3–4: Assessment & Planning

Goals:

• Identify quick wins in leadership enablement or alignment
• Start mapping current org challenges and friction points

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Activities:

• Launch a short “Leadership Feedback Pulse” survey or 1:1 interviews
• Audit current leadership development programs (if any)
• Sit in on all active cross-functional initiatives

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Deliverables:

• Leadership Systems Map (how communication, planning, and coaching currently work)
• 30/60/90-Day Roadmap of initiatives

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Month 2: Activation

Goals:

• Begin owning key rituals and projects
• Launch our first leadership enablement initiative

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Activities:

• Facilitate first executive offsite or strategic sync
• Introduce new ritual (e.g., team retros, strategic standups, async updates)
• Coach 1–2 directors or execs through a leadership growth plan

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Deliverables:

• Executive Team Dashboard (accountability, alignment, energy)
• Retrospective facilitation guide or leadership ritual template

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Month 3: Impact & Expansion

Goals:

• Demonstrate leverage across CEO, exec team, and organization
• Build systems that will scale beyond me

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Activities:

• Finalize and roll out a Leadership Operating System (LOS)
• Co-create a “CEO Time Audit” and design time reallocation plan
• Build succession or promotion path for internal team leaders

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Deliverables:

• “Strategic Partner Impact Memo” — what’s changed, what’s next
• Coaching Library or internal Leadership Playbook draft
• Roadmap for next 6 months of strategic priorities

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Success Metrics by Day 90

• CEO reports >30% time reclaimed for strategic work
• 2+ leadership development initiatives launched
• Executive team alignment rating improves 10–20%
• First cohort of leaders activated in growth or coaching journey

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Beyond This Role

I’ve spent 25 years wearing a lot of hats: strategy, ops, community, product, growth, fundraising, and more. I’ve coached over 1,200 leaders, built scalable systems, and helped companies move from chaos to clarity.

If there’s something you need done to help your people or systems lead better, just ask. Chances are, I’ve done it. And if not, I’ll learn it fast.

Stay Curious,
​Thomas Knoll