Where I help

Where I help

Where I help

Startups tend to break in predictable ways as they grow. I’m usually called in at those inflection points to steady execution and rebuild momentum.

As a Strategic Advisor, I design the system and coach your team through implementation. As a Fractional Executive, I step in to own outcomes and drive execution until things run smoothly again. We dial the level of involvement up or down as the company’s needs change—finding the right blend of support for where you are right now.

Below are the inflection points where I’m most often called in and how I plug in to fix them.

Startups tend to break in predictable ways as they grow. I’m usually called in at those inflection points to steady execution and rebuild momentum.

As a Strategic Advisor, I design the system and coach your team through implementation. As a Fractional Executive, I step in to own outcomes and drive execution until things run smoothly again. We dial the level of involvement up or down as the company’s needs change—finding the right blend of support for where you are right now.

Below are the inflection points where I’m most often called in and how I plug in to fix them.

Everything Takes Too Long

Everything takes three times longer than it should. You need systems, workflows, and infrastructure that let the company run without constant firefighting—OKRs, dashboards, hiring processes, financial controls, and the operating rhythms that turn chaos into momentum.

Everything takes three times longer than it should. You need systems, workflows, and infrastructure that let the company run without constant firefighting—OKRs, dashboards, hiring processes, financial controls, and the operating rhythms that turn chaos into momentum.

What This Might Look Like


  • Install your first operating system: OKRs, dashboards, reporting rhythms

  • Design and implement exec/board meeting cadence and materials

  • Create scalable processes and workflows for growth

  • Implement systems so growth doesn’t create chaos

  • Build repeatable hiring, onboarding, and performance management systems

  • Establish financial visibility and controls

  • Stand up financial and operational dashboards

  • Fix bottlenecks: finance, HR, legal, compliance, revenue ops

  • Build data infrastructure: dashboards, metrics, reporting

  • Develop hands-on frameworks and playbooks

What This Might Look Like


  • Install your first operating system: OKRs, dashboards, reporting rhythms

  • Design and implement exec/board meeting cadence and materials

  • Create scalable processes and workflows for growth

  • Implement systems so growth doesn’t create chaos

  • Build repeatable hiring, onboarding, and performance management systems

  • Establish financial visibility and controls

  • Stand up financial and operational dashboards

  • Fix bottlenecks: finance, HR, legal, compliance, revenue ops

  • Build data infrastructure: dashboards, metrics, reporting

  • Develop hands-on frameworks and playbooks

What This Might Look Like


  • Deep product and customer knowledge

  • Long-term vision and emotional stake

  • Ability to pivot and innovate

  • Relentless ownership mindset

Strategic Advisor: Design the operating system with you and advise on implementation
Fractional Executive: Build and run the systems myself, stand up the infrastructure

Strategic Advisor: Design the operating system with you and advise on implementation
Fractional Executive: Build and run the systems myself, stand up the infrastructure

If I Stop, Everything Stops

You’re still the engine behind everything. Every decision, every problem, every next step. It’s not sustainable. The challenge isn’t just delegation, it’s learning to lead through others, putting systems in place that work without you, and making the shift from doing to directing without losing what makes the company yours.

You’re still the engine behind everything. Every decision, every problem, every next step. It’s not sustainable. The challenge isn’t just delegation, it’s learning to lead through others, putting systems in place that work without you, and making the shift from doing to directing without losing what makes the company yours.

What This Might Look Like


  • Free founder from firefighting to focus on moving forward

  • Act as founder’s right hand for operational complexity

  • Stabilize operations when founder is overloaded

  • Take over decision fatigue and day-to-day operational complexity

  • Map delegation strategy and coach through letting go

What This Might Look Like


  • Free founder from firefighting to focus on moving forward

  • Act as founder’s right hand for operational complexity

  • Stabilize operations when founder is overloaded

  • Take over decision fatigue and day-to-day operational complexity

  • Map delegation strategy and coach through letting go

What This Might Look Like


  • Deep product and customer knowledge

  • Long-term vision and emotional stake

  • Ability to pivot and innovate

  • Relentless ownership mindset

Strategic Advisor: Coach you through letting go and design what you delegate
Fractional Executive: Take things off your plate immediately and own the operations

Strategic Advisor: Coach you through letting go and design what you delegate
Fractional Executive: Take things off your plate immediately and own the operations

I Know How to Build Product — Not a Company

You know how to build product, but building the company that scales it is a completely different skill set. And no one teaches you how. Building a product = making something people want. Building a company = creating the human + structural system that can keep delivering value at scale.

You know how to build product, but building the company that scales it is a completely different skill set. And no one teaches you how. Building a product = making something people want. Building a company = creating the human + structural system that can keep delivering value at scale.

What This Might Look Like


  • Guide shift from building product to building company

  • Establish company-building discipline

  • Design company to scale (mindset and structure)

  • Create structure, roles, and rhythms so the business runs with consistency when you step back

  • Show how to distribute decisions effectively without micromanaging

  • Organize the foundational structure and systems of the company

What This Might Look Like


  • Guide shift from building product to building company

  • Establish company-building discipline

  • Design company to scale (mindset and structure)

  • Create structure, roles, and rhythms so the business runs with consistency when you step back

  • Show how to distribute decisions effectively without micromanaging

  • Organize the foundational structure and systems of the company

What This Might Look Like


  • Deep product and customer knowledge

  • Long-term vision and emotional stake

  • Ability to pivot and innovate

  • Relentless ownership mindset

Strategic Advisor: Guide the mental shift and design the foundation with you
Fractional Executive: Build the company structure while you stay focused on product

Strategic Advisor: Guide the mental shift and design the foundation with you
Fractional Executive: Build the company structure while you stay focused on product

Growth Is Breaking What Worked Before

The org structure doesn’t work at this size, groups aren’t aligned, early leaders are hitting their limits, and culture is fraying. You need to redesign the company for scale before it collapses under its own success.

The org structure doesn’t work at this size, groups aren’t aligned, early leaders are hitting their limits, and culture is fraying. You need to redesign the company for scale before it collapses under its own success.

What This Might Look Like


  • Scale founder-based leadership from 1–200+

  • Design and optimize exec team structure and fit

  • Design org structure: who to hire next, when to add layers, how reporting lines evolve

  • Professionalize HR and performance systems

  • Build cross-functional alignment across functions

  • Implement unified operating cadence across departments

  • Support leadership stretch: help early managers step up or add layers

  • Preserve culture during rapid headcount growth

What This Might Look Like


  • Scale founder-based leadership from 1–200+

  • Design and optimize exec team structure and fit

  • Design org structure: who to hire next, when to add layers, how reporting lines evolve

  • Professionalize HR and performance systems

  • Build cross-functional alignment across functions

  • Implement unified operating cadence across departments

  • Support leadership stretch: help early managers step up or add layers

  • Preserve culture during rapid headcount growth

What This Might Look Like


  • Deep product and customer knowledge

  • Long-term vision and emotional stake

  • Ability to pivot and innovate

  • Relentless ownership mindset

Strategic Advisor: Design the scaling architecture and advise leadership through transition
Fractional Executive: Build the systems, run cross-functional alignment, layer the leadership

Strategic Advisor: Design the scaling architecture and advise leadership through transition
Fractional Executive: Build the systems, run cross-functional alignment, layer the leadership

The People Stuff Is Draining Me

The high-stakes dynamics that no playbook covers: cofounder conflict, exec exits, team friction, tough investor relations, board politics, hiring your first executive. The moments that can sink the company if handled wrong.

The high-stakes dynamics that no playbook covers: cofounder conflict, exec exits, team friction, tough investor relations, board politics, hiring your first executive. The moments that can sink the company if handled wrong.

What This Might Look Like


  • Hire your first non-founding executive

  • Manage founder exits

  • Manage leadership team member exits

  • Handle board member onboarding and exits

  • Navigate and resolve leadership team friction

  • Address and resolve cofounder conflict

  • Set up Founder/CEO and COO combo for success

  • Navigate tough investor relations

  • Navigate complex strategic relationships and partnerships

  • Mediate high-stakes interpersonal dynamics

  • Optimize exec team structure and fit

What This Might Look Like


  • Hire your first non-founding executive

  • Manage founder exits

  • Manage leadership team member exits

  • Handle board member onboarding and exits

  • Navigate and resolve leadership team friction

  • Address and resolve cofounder conflict

  • Set up Founder/CEO and COO combo for success

  • Navigate tough investor relations

  • Navigate complex strategic relationships and partnerships

  • Mediate high-stakes interpersonal dynamics

  • Optimize exec team structure and fit

What This Might Look Like


  • Deep product and customer knowledge

  • Long-term vision and emotional stake

  • Ability to pivot and innovate

  • Relentless ownership mindset

Strategic Advisor: Coach you through the dynamics and strategy for resolution
Fractional Executive: Step in directly to mediate, restructure, and manage the transition

Strategic Advisor: Coach you through the dynamics and strategy for resolution
Fractional Executive: Step in directly to mediate, restructure, and manage the transition

 I Don’t Know How to Lead at This Level

You need to leap from hands-on founder to CEO who leads through others. And your early team needs to evolve too—from scrappy operators to leaders who can own functions, build teams, and scale without you running everything.

You need to leap from hands-on founder to CEO who leads through others. And your early team needs to evolve too—from scrappy operators to leaders who can own functions, build teams, and scale without you running everything.

What This Might Look Like


  • Guide Founder → CEO transition

  • Teach how to lead through others without losing vision or control

  • Coach managers and install leadership layers

  • Coach new leaders to scale, not just manage

  • Build exec team trust, alignment, and performance cadences

  • Create scalable people processes: hiring, onboarding, feedback

  • Develop leadership team structure and fit

  • Install performance management that develops leaders

  • Leadership development and team building

  • Decision-making and problem-solving for leadership

What This Might Look Like


  • Guide Founder → CEO transition

  • Teach how to lead through others without losing vision or control

  • Coach managers and install leadership layers

  • Coach new leaders to scale, not just manage

  • Build exec team trust, alignment, and performance cadences

  • Create scalable people processes: hiring, onboarding, feedback

  • Develop leadership team structure and fit

  • Install performance management that develops leaders

  • Leadership development and team building

  • Decision-making and problem-solving for leadership

What This Might Look Like


  • Deep product and customer knowledge

  • Long-term vision and emotional stake

  • Ability to pivot and innovate

  • Relentless ownership mindset

Strategic Advisor: Guide you and your leadership team through the evolution
Fractional Executive: Develop your leaders hands-on and build the systems that scale them

Strategic Advisor: Guide you and your leadership team through the evolution
Fractional Executive: Develop your leaders hands-on and build the systems that scale them

When I Hit Capacity, the Company Stalls

You’re drowning in firefighting and decisions only you can make. Every time you hit your limit, momentum slows—or stops altogether. I step in as your right hand: taking ownership of operational complexity, keeping the business moving forward, and freeing you to focus on product, vision, and leadership.

You’re drowning in firefighting and decisions only you can make. Every time you hit your limit, momentum slows—or stops altogether. I step in as your right hand: taking ownership of operational complexity, keeping the business moving forward, and freeing you to focus on product, vision, and leadership.

What This Might Look Like


  • Step into critical gaps—from leading acquisitions and integrations to owning ops/finance/HR temporarily until the right exec is hired

  • Handle complex projects: expansion, compliance, partnerships

  • Drive cross-functional execution

  • Take on projects with no natural owner: regulatory, vendor negotiations, investor reporting

  • Provide leadership scale without permanent overhead

What This Might Look Like


  • Step into critical gaps—from leading acquisitions and integrations to owning ops/finance/HR temporarily until the right exec is hired

  • Handle complex projects: expansion, compliance, partnerships

  • Drive cross-functional execution

  • Take on projects with no natural owner: regulatory, vendor negotiations, investor reporting

  • Provide leadership scale without permanent overhead

What This Might Look Like


  • Deep product and customer knowledge

  • Long-term vision and emotional stake

  • Ability to pivot and innovate

  • Relentless ownership mindset

Strategic Advisor: Help you scope the project and decide who should own it
Fractional Executive: Own and deliver the project myself

Strategic Advisor: Help you scope the project and decide who should own it
Fractional Executive: Own and deliver the project myself

I’m Not Showing Up Strong in Front of My Board and Investors

Without discipline and clear reporting, every board meeting feels like defense instead of leadership. I build the oversight, metrics, and prep that earn investor confidence and get you ready for fundraising, diligence, or exit.

Without discipline and clear reporting, every board meeting feels like defense instead of leadership. I build the oversight, metrics, and prep that earn investor confidence and get you ready for fundraising, diligence, or exit.

What This Might Look Like


  • Build financial discipline and oversight

  • Set the board up for success, including proper governance

  • Build fundraising readiness: metrics, decks, data room, story

  • Stand up effective board reporting and fundraising prep

  • Build data infrastructure for decision-making

  • Create dashboards that prove operational maturity

  • Prepare the company for exit or acquisition

  • Manage the sale of the company

  • Give investors confidence through operational excellence

What This Might Look Like


  • Build financial discipline and oversight

  • Set the board up for success, including proper governance

  • Build fundraising readiness: metrics, decks, data room, story

  • Stand up effective board reporting and fundraising prep

  • Build data infrastructure for decision-making

  • Create dashboards that prove operational maturity

  • Prepare the company for exit or acquisition

  • Manage the sale of the company

  • Give investors confidence through operational excellence

What This Might Look Like


  • Deep product and customer knowledge

  • Long-term vision and emotional stake

  • Ability to pivot and innovate

  • Relentless ownership mindset

Strategic Advisor: Design the metrics framework and coach you through board dynamics
Fractional Executive: Build the dashboards, own board reporting, run fundraising prep

Strategic Advisor: Design the metrics framework and coach you through board dynamics
Fractional Executive: Build the dashboards, own board reporting, run fundraising prep

I Can’t Keep Masking, It’s Exhausting Me

For founders on the autism spectrum: the usual playbook assumes neurotypical wiring and it doesn’t fit. You’re constantly translating yourself, often misunderstood, and operating in a world not designed for you. The cognitive load is exhausting. You need to build a company that works with your wiring, not against it, so you can lead authentically and scale without burning out.

For founders on the autism spectrum: the usual playbook assumes neurotypical wiring and it doesn’t fit. You’re constantly translating yourself, often misunderstood, and operating in a world not designed for you. The cognitive load is exhausting. You need to build a company that works with your wiring, not against it, so you can lead authentically and scale without burning out.

What This Might Look Like


  • Understand your wiring: uncover how you’re wired, clarify strengths/sensitivities, and create a shared language others can work with.

  • Anticipate and reduce friction: spot where misalignments will show up (board, team, investors) and design practices that ease the load.

  • Translate and bridge: act as your sounding board (“WTF is wrong with humans?”), translate you to others (and others to you), and step in when communication breaks down.

  • Build systems that fit you: design company practices and rhythms around your wiring, reducing cognitive load while still scaling.

  • Support resilience: help regulate during overwhelm, update “human simulation software,” and teach repair skills when things go sideways.

  • Shape sustainable leadership: ensure you’re not held back by mismatched expectations, and create space to lead authentically and reduce masking.

What This Might Look Like


  • Understand your wiring: uncover how you’re wired, clarify strengths/sensitivities, and create a shared language others can work with.

  • Anticipate and reduce friction: spot where misalignments will show up (board, team, investors) and design practices that ease the load.

  • Translate and bridge: act as your sounding board (“WTF is wrong with humans?”), translate you to others (and others to you), and step in when communication breaks down.

  • Build systems that fit you: design company practices and rhythms around your wiring, reducing cognitive load while still scaling.

  • Support resilience: help regulate during overwhelm, update “human simulation software,” and teach repair skills when things go sideways.

  • Shape sustainable leadership: ensure you’re not held back by mismatched expectations, and create space to lead authentically and reduce masking.

What This Might Look Like


  • Deep product and customer knowledge

  • Long-term vision and emotional stake

  • Ability to pivot and innovate

  • Relentless ownership mindset

Strategic Advisor: Navigate people dynamics, design systems that fit your wiring, coach leadership/board on working with you
Fractional Executive: Act as translator and bridge, build systems around you, mediate when needed, train your team

Strategic Advisor: Navigate people dynamics, design systems that fit your wiring, coach leadership/board on working with you
Fractional Executive: Act as translator and bridge, build systems around you, mediate when needed, train your team

How to Work With Me

How to Work With Me

Strategic Advisor Engagements


  • When you need a thinking partner

  • Monthly or bi-weekly strategic sessions

  • On-call for high-stakes decisions and critical moments

  • I design the architecture, you and your team implement with my guidance

  • Lower time commitment, outsized leverage where it matters most

Strategic Advisor Engagements


  • When you need a thinking partner

  • Monthly or bi-weekly strategic sessions

  • On-call for high-stakes decisions and critical moments

  • I design the architecture, you and your team implement with my guidance

  • Lower time commitment, outsized leverage where it matters most

Strategic Advisor Engagements


  • Valuation Growth (2023): Founder-led startups grew by 22.4% vs 4.7% for non-founder-led ones (PitchBook).

  • Innovation: Founder-led firms generate 31% more patents (HBR).

  • Exit Performance: 73% of $1B+ exits were founder-led (Tamaseb).

  • Capital Efficiency: Founders raise less and deliver more ROI (a16z).

Fractional Executive Engagements


  • When you need another operator in the room

  • ~ 1-3 days per week embedded with your team

  • I build and run the systems, own outcomes, deliver results

  • Hands-on execution across multiple functions

  • Higher time commitment, direct operational relief and momentum

Fractional Executive Engagements


  • When you need another operator in the room

  • ~ 1-3 days per week embedded with your team

  • I build and run the systems, own outcomes, deliver results

  • Hands-on execution across multiple functions

  • Higher time commitment, direct operational relief and momentum

Fractional Executive Engagements


  • Valuation Growth (2023): Founder-led startups grew by 22.4% vs 4.7% for non-founder-led ones (PitchBook).

  • Innovation: Founder-led firms generate 31% more patents (HBR).

  • Exit Performance: 73% of $1B+ exits were founder-led (Tamaseb).

  • Capital Efficiency: Founders raise less and deliver more ROI (a16z).

You don’t have to know upfront which model is right. We’ll shape the engagement around what the company actually needs and adjust as it evolves. Sometimes that means pure advising, sometimes full-on fractional leadership, and often it’s a hybrid in between. I might be hands-on in one area while staying high-level in another.

You don’t have to know upfront which model is right. We’ll shape the engagement around what the company actually needs and adjust as it evolves. Sometimes that means pure advising, sometimes full-on fractional leadership, and often it’s a hybrid in between. I might be hands-on in one area while staying high-level in another.


Let's talk about what you're facing and figure out the right fit.


Let's talk about what you're facing and figure out the right fit.

All rights reserved © 2024 dawnumlah.com

All rights reserved © 2024 dawnumlah.com

All rights reserved © 2024 dawnumlah.com

All rights reserved © 2024 dawnumlah.com