FRACTIONAL CFO · CHICAGO · TRANSFORMATION AND M&A OPERATOR

Three exits. Deliberate practice.

FRACTIONAL CFO · CHICAGO · TRANSFORMATION AND M&A OPERATOR

Three exits. Deliberate practice.

Why Fractional. Why This.

The deliberate choice to stay.

Most fractional CFOs couldn't get the full-time seat. Sierra left it - three times, successfully, on her own terms. The fractional model isn't a fallback. It's the right structure for the work: deep engagement, real accountability, and the freedom to choose clients worth building for.

Every engagement adds something that wasn't there before - that's the name and the promise. A business assessed honestly. A leadership team aligned on what matters. Financial infrastructure that holds up under scrutiny. And, when the time comes, a transaction that closes.

CMA Certified^Expert in Residence^LP Investor^Midwest Roots

I

Operating CFO Through Three Exits

Acquisitions to YouGov, TransUnion, and Discovery Communications - as the CFO in the seat, not an outside advisor. Sierra was brought in to assess the business, align leadership on strategic priorities, and build the financial and operational infrastructure from the ground up. That work included partnering with technical teams on Infosec compliance, co-developing the CIP narrative with business leaders and bankers, and building the story that acquirers ultimately bought.

Then, when the process started, she owned it: data room, 209+ personally-managed diligence items across finance, legal, HR, and IP, NWC peg negotiation, SALT analysis, disclosure schedules, and closing waterfall. That scope - and that accountability - is the distinction that matters when the next exit is yours.

II

This Model Is a Choice, Not a Default

Full-time CFO roles are available. Fractional is the decision - because it means working only with companies worth building, going deeper with fewer clients, and measuring success by outcomes, not tenure.

III

You Get Sierra. Not a Team.

No analysts doing the work while a senior partner takes the meetings. Every engagement is led directly by Sierra - the same person in the board room and in the model.

IV

Breadth That Full-Time Can't Offer

SaaS, marketplace, media, AdTech, HCM - and global operations across 19 countries. Having seen more business models means faster pattern recognition and fewer expensive mistakes for your company.

V

The Investor Perspective - From Both Sides

As a Limited Partner at Service Provider Capital and Expert in Residence at 1871, Sierra operates inside the investor ecosystem, not just adjacent to it. That means founders get a CFO who understands how investors think, and VCs get diligence work from someone who has actually run the companies they're evaluating.

What We Build Together

Strategic Finance

FP&A & Financial Modeling

A fully built financial operating system: models, budgets, forecasts, and KPI dashboards that power real decisions.

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Drivers-based financial models
Annual budget & rolling forecasts
Board & investor reporting packages
SaaS unit economics & cohort analysis

Capital Markets

Strategic Finance

Capital Raise Preparation

From pre-seed through Series C: financial materials, data rooms, and narratives that give investors confidence and accelerate close.

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Pitch deck financial section
Data room setup & management
Financial narrative & projections
Due diligence support

Transactions

Strategic Finance

Transactions

M&A & Exit Readiness

Three exits built. We know exactly what acquirers scrutinize, what kills deals, and how to position your company for maximum value.

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Assessment, alignment, incl. Infosec
CIP narrative & exit readiness
Data room and diligence ownership
NWC peg, SALT & disclosure schedules

Compliance

Transactions

Accounting Infrastructure

GAAP-compliant financials, tight close processes, and audit readiness that build the credibility your next financing round demands.

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Revenue recognition (ASC 606)
Month-end close optimization
Audit preparation & management
Accounting systems implementation

Global Ops

Compliance

Global Ops

International Operations

International expansion, multi-entity structures, and cross-border compliance from an operator who has built global finance from the inside.

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International entity setup
Multi-currency reporting
Transfer pricing frameworks
Cross-border treasury management

Advisory

Compliance

Global Ops

CFO-as-Advisor

Strategic counsel on-demand for board prep, deal decisions, and critical financial strategy - without a full fractional engagement.

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Monthly advisory retainer
Board meeting preparation
Finance team mentorship
Strategic deal review

Engagements are selective: Sierra works with a limited number of companies at a time to ensure full attention, not a fraction of it. Clients are growth-stage founders preparing for a raise or exit, and VC/PE investors who need an operator - not just an analyst - evaluating potential acquisitions and supporting portfolio companies.

Learn More

For Venture Capital & Investors

Most operating partners come from IB or consulting. Sierra built companies and sold them as CFO.

In each of her three acquisitions, Sierra came in not to execute a transaction, but to improve the business - assess what was working, align leadership on priorities, build the financial and operational infrastructure, achieve compliance certifications, and co-develop the narrative that acquirers bought. Then she owned the transaction.

That's what makes Additive Insights useful to VC and PE firms at the moments it matters most: before you close, when you need an operator's lens on what a target really is, and after you close, when your portcos need a CFO who can assess, align, and build - not just report. As a single operator, Sierra owns finance, legal, HR, and compliance. Fewer advisors in the room. Full accountability for outcomes.

Acquisition Target Assessment
Portfolio CFO-in-Residence
Project Based Portco Engagement

By Stage - The Right Support at Every Level

Pre-Revenue / Seed

Build it right from the start - before bad habits become expensive problems.

Early decisions about chart of accounts, entity structure, and reporting cadence shape everything that follows. We help founders put the right infrastructure in place before it becomes urgent - and build the financial story that gets the first institutional check written.

▸ Financial model & projections for seed raise

▸ Accounting foundation & bookkeeping oversight

▸ Cap table & equity compensation strategy

▸ Cash flow management & burn analysis

▸ Pitch deck financial narrative

Series A

Translate traction into institutional-grade financial infrastructure.

Series A investors want to see that you understand your unit economics, can forecast with confidence, and have a finance function that scales. We build the reporting, metrics, and narrative that gets the deal done and sets up the next round.

▸ SaaS metrics dashboard (ARR, MRR, churn, CAC, LTV)

▸ Annual operating plan & quarterly reforecasting

▸ Board reporting package & investor updates

▸ Revenue recognition & GAAP compliance

▸ Finance team hiring plan & first hire criteria

Series B+

Operate at institutional scale.

Multi-product, multi-market, and multi-entity complexity requires a CFO function that's ahead of the business — not catching up to it. We build the infrastructure that supports scale: FP&A systems, international expansion, and the financial story that positions you for a strategic outcome.

▸ Multi-entity consolidation & international reporting

▸ Operational KPI framework & department-level budgeting

▸ Strategic finance support for M&A evaluation

▸ Investor relations & secondary market preparation

▸ Executive team financial fluency coaching

Exit Preparation

Three companies transformed. Three exits executed from the operators seat.

The outcome is decided well before the process starts. The work begins with an honest assessment of the business - what's working, what isn't, what a buyer will find. It continues through leadership alignment, compliance certifications, and the co-development of the narrative that acquirers buy. Then, when the process starts, we own every workstream through close. Start 12–24 months before you plan to run a process.

▸ Business assessment & gap diagnotic

▸ Leadership alignment on strategic priorities

▸ SOCII Type 2 / ISO 27001 preparation with technical team

▸ CIM narrative co-development with business leaders and bankers

▸ Exit readiness assessment & gap remediation

▸ Quality of earnings preparation & FDD response
▸ Data room build, management & diligence ownership
▸ NWC peg negotiation & closing waterfall
▸ SALT exposure analysis & indemnification strategy
▸ HR, employment & IP diligence management

▸ Disclosure schedule preparation

▸ Integration planning & Day 1 continuity

Sierra Hinson Founder · Fractional CFO & Operating Advisor

With 19 years in the Chicago tech ecosystem, Sierra has served as CFO, VP Finance, and interim finance leader across more than a dozen growth-stage technology companies - guiding three through successful strategic acquisitions: Curiosity.com to Discovery Communications, Signal Digital to TransUnion, and KnowledgeHound to YouGov. In each company, she was brought in not to prepare for a transaction, but to improve the business. That work included assessing the business honestly, aligning leadership on strategic priorities, building the financial and operational infrastructure from the ground up, partnering with technical teams on SOC II Type 2 and ISO 27001 compliance, and co-developing the acquisition narrative with business leaders and bankers - the story that acquirers ultimately bought. Then, when the process started, she owned it: 209+ personally-managed diligence items across finance, legal, HR, and IP; NWC peg negotiation; SALT analysis; disclosure schedules; and closing waterfall.

Her career spans childcare marketplaces to influencer platforms to customer intelligence - from Sittercity's early Momentum Award days through Signal Digital's $60M revenue year. Scaling companies from first dollar to exit is the work. Sierra brings deep SaaS expertise, international operations experience, and a strong pattern-recognition advantage from working across more than a dozen Midwest tech companies. She serves as Expert in Residence at 1871 and is a Limited Partner at Service Provider Capital.

The fractional model was a deliberate choice made after three successful exits - not a fallback between roles. It's the structure that allows genuine depth with a small number of clients, accountability measured by transformation and outcomes, and the freedom to only work with companies and founders worth building for.

Increasingly, Sierra's work extends to the investor side - providing acquisition target assessment and transformation advisory for VC firms and PE sponsors evaluating growth-stage companies. It's the natural evolution: three exits from the operator seat - with full accountability for finance, HR, legal, and compliance - now applied to help investors find and evaluate the next ones and build them toward the same outcomes.

Certification: CMA - Certified Management Accountant

Community Role: Expert in Residence, 1871 Chicago

Investment: Limited Partner, Service Provider Capital

Based In: Chicago, IL - in the ecosystem since 2007

What Leaders Say...

★★★★★

"Sierra is a CEO and CRO's secret weapon. I've seen firsthand the critical role she plays in scaling and exiting a business - she's incredibly versatile, wired for growth, and clears the way for companies to reach their full potential."

CRO, KnowledgeHound

★★★★★

"I've worked with Sierra at multiple companies and would work with her again without hesitation. She's an incredible partner, a talented financial steward, and someone who makes every business she touches better."

CEO, Signal Digital, Curiosity.com, & brick&batten

★★★★★

"Sierra was a key player as we built Pear. Her command of both finance and operations let her contribute far more value than any single role would suggest. I'd jump at the opportunity to work with her again."

CEO, Pear

★★★★★

"I really enjoyed working with Sierra. She is incredibly smart and dedicated. Sierra brought both creativity and a practical approach to her role at Sittercity. She was very talented at identifying opportunities for growth and cost saving, leading analytics, and developing coherent recommendations. I hopt to work with her again!"

President, Sittercity

Three exits. Deliberate practice.

Three exits. Deliberate practice.

Finance That Adds Value

Companies We've Worked With

Why Fractional. Why This.

The deliberate choice to stay.

CMA Certified^Expert in Residence^LP Investor^Midwest Roots

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II

III

IV

V

What We Build Together

Strategic Finance

Strategic Finance

Strategic Finance

Capital Markets

Strategic Finance

Strategic Finance

Transactions

Strategic Finance

Transactions

Compliance

Compliance

Transactions

Global Ops

Compliance

Global Ops

Advisory

Compliance

Global Ops

For Venture Capital & Investors

Most operating partners come from IB or consulting. Sierra built companies and sold them as CFO.

By Stage - The Right Support at Every Level

Pre-Revenue / Seed

Series A

Series B+

Exit Preparation

Sierra Hinson Founder · Fractional CFO & Operating Advisor

What Leaders Say...

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★★★★★

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Let's have an honest conversation.

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