Finance That Adds Value
After guiding three companies through strategic acquisitions to YouGov, TransUnion, and Discovery Communications, Sierra Hinson chose fractional practice intentionally. Not as a stepping stone. As the model that best serves growth-stage companies and the people building them.
Companies We've Worked With
KnowledgeHound → YouGov | Signal Digital → TransUnion | Curiosity.com→ Discovery Communications| Sittercity | Pear | Public Good | Inventables | Popular Pays | brick&batten | Globalli | All Planet | Blinc | RM
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. Sharper unit economics. A financial narrative that holds up to acquirer scrutiny. Infrastructure that scales past the next round.
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. That distinction is the one 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
Strategic Finance
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
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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- Exit strategy development
- Quality of earnings preparation
- Financial due diligence response
- Integration planning support
Compliance
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's eye on potential acquisitions.
For Venture Capital & Investors
Most operating partners come from IB or consulting. Sierra has built companies and sold them as CFO.
That distinction - operator, not consultant - is what makes Additive Insights useful to VC and PE firms at the moment it matters most: before you close, when the financial picture is still forming, and after you close, when your portcos need a CFO function they can't yet afford to hire full-time.
- 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 exits built from the operator seat.
We know exactly what acquirers scrutinize, what kills deals at the last minute, and how to position your financials and narrative for maximum value. Start 12–18 months before you plan to run a process.
▸ Exit readiness assessment
▸ Quality of earnings preparation
▸ CIM financial support
▸ Data room build & management
▸ Acquirer due diligence response
▸ Integration planning support
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.
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 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 financial due diligence for VC firms and PE sponsors evaluating growth-stage companies. It's the natural evolution: three exits from the operator seat, now applied to help investors find and evaluate the next ones.
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...
★★★★★
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"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
★★★★★
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"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
★★★★★
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"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
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"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
Let's have an honest conversation.
Whether you're a founder building toward a raise or exit, or an investor evaluating an acquisition - most engagements start the same way: a direct 30-minute conversation about what you're trying to accomplish and whether this is the right fit.
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