Assessed. Aligned. Built to Exit.

Assessed. Aligned. Built to Exit.Assessed. Aligned. Built to Exit.Assessed. Aligned. Built to Exit.

  ENTERPRISE VALUE, BUILT FROM THE INSIDE

Series A to Exit

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Your (Embedded) Operating Partner

Sierra embeds inside growth-stage technology companies and takes ownership of the infrastructure that determines enterprise value - accounting, finance, HR, legal, and compliance. The work is additive: increasing revenue, improving efficiency, and protecting the multiple. Three exits are the proof.

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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 This Model. Why This Scope.

The deliberate choice to go deeper.

This model is a deliberate choice - the structure required for the work.


Deep engagement with a small number of companies. Full accountability for outcomes. The ability to choose situations where building something materially better is possible.


Every engagement leaves the business different than it was found:

  • Revenue architecture that reflects the value actually delivered
  • Cost structures aligned to reality
  • Contracts drafted and standardized, not patched
  • Organizations designed to execute, not just grow
  • Operational infrastructure that holds up under diligence


And when the process starts, a transaction that closes.


When founders and investors exit well, that capital funds the next company, the next team, the next generation. That flywheel is the point.

CMA Certified ^ Expert in Residence ^ LP Investor ^ Midwest

I

Three Exits - From the Operator’s Seat 

Acquisitions to YouGov, TransUnion, and Discovery Communications - brought in each time to improve business outcomes and chart the path to exit. Sierra took ownership of accounting, finance, HR, legal, and compliance from inside each company. That work included rebuilding pricing architectures, restructuring cost bases, designing organizations and cascading strategic objectives through every department, drafting and negotiating contracts directly, leading cross-functional compliance initiatives, partnering with technical teams on SOC II and infrastructure optimization, and co-developing the CIP narrative that acquirers ultimately bought.


Then, when the process started, she owned it: data room, 209 personally-managed diligence items across accounting, finance, legal, HR, compliance, and IP - representing 65-80% of the total diligence workload - NWC peg negotiation, SALT analysis, disclosure schedules drafted in-house, and closing waterfall. That scope - and that accountability - is the difference between supporting a transaction and owning one.

II

This Model Is a Choice, Not a Default

Full-time executive roles are available. This model is the decision - because it means working only with companies worth building, going deeper with fewer clients, and measuring success by outcomes, not tenure. The CFOO scope - finance, HR, legal, and compliance owned by one person - is the combination most growth-stage companies need and can’t hire separately.  This is not a capacity model. It’s an outcomes model.

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 - No analysts. No layers. No handoffs. The same person builds the model, runs the function, and sits across from buyers in diligence.

IV

Breadth That Full-Time Can't Offer

SaaS, marketplace, media, AdTech, HCM - and direct operational ownership across 17 countries. Pricing architecture at a B2B analytics platform. Data-driven growth at a consumer marketplace. $20M cost restructuring at an adtech company. Multi-variable margin optimization at a sponsorship platform. International entity management from the US to Japan to the Netherlands to South Africa. Operating across multiple business models creates pattern recognition: where enterprise value is created, and where it leaks. Most of that isn’t visible in reporting - it shows up in diligence.

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. Founders get a CFOO who understands how investors evaluate companies. VCs get an operator who has built and exited the companies they’re evaluating - not an advisor who has reviewed them from the outside. Fewer advisors in the room. One operator accountable for outcomes.

What We Build Together

The work is structured around outcomes - not functions. These are the systems that determine enterprise value.

Revenue & Strategic Finance

Build the Base 

Revenue is the primary driver of enterprise value - but only if it’s structured correctly. Revenue architecture, unit economics, and the financial infrastructure that tells the real growth story - to investors, board members, and eventually buyers. 

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  • Pricing architecture: ACV optimization, packaging strategy, value-based pricing  
  • Revenue recognition (ASC 606) and ARR methodology: documented and defensible 
  • Unit economics framework: CAC, LTV, payback by channel, cohort analysis 
  • Customer cube: every customer, every product, every dollar, every renewal 
  • Drivers-based financial models, annual plans, and rolling forecasts 
  • Board and investor reporting packages: investor-grade, consistent, delivered on schedule 
  • Capital raise preparation: financial model, narrative, data room (Seed → Series D) 

Efficiency & Operations

Improve the Margin 

Margin is designed, not discovered. Financial infrastructure, organizational design, and operational alignment that keep the business running efficiently - and produce the reporting that institutional stakeholders require. 

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  • Finance function build: close process, chart of accounts, ERP selection and implementation 
  • Organizational design: headcount planning, role definition, OKR/KPI cascade 
  • Vendor and contract management: terms standardization, renegotiation, cost review 
  • Compensation architecture: equity grants, 409a compliance, management incentive design 
  • Cloud infrastructure and technology cost assessment with engineering teams 
  • International operations: multi-entity consolidation, transfer pricing, cross-border compliance
  • SALT nexus analysis and compliance 
  • SOC II / ISO 27001 readiness with your technical team 

Risk & Exit Readiness

Protect the Multiple 

Risk is what buyers price. This is where multiples are won or lost. The functions I own - accounting, finance, HR, legal, and compliance - represent 65-80% of the diligence workload in a growth-stage technology transaction. Every gap discovered before a process is preparation. Every gap discovered during a process is a price reduction. 

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  • Business diagnostic: what a buyer will find before they do 
  • Contract book review and standardization: MFN clauses, termination rights, inconsistent terms 
  • IP assignment chain: every founder, employee, and contractor documented 
  • Employment documentation audit: agreements drafted, signed, filed, and current  
  • CIP narrative co-development: the story a buyer uses to justify the acquisition 
  • Data room build: substantially complete before LOI
  • Management team preparation for FDD sessions and buyer presentations 
  • GDPR, CCPA, and regulatory compliance initiatives 

Transaction Execution

Single Point of Accountability Through Close 

When the process starts, I own it end-to-end - across every non-technical workstream. 209 diligence items personally owned on the last deal. 83 closed in the peak week - while the business kept running. One person across every non-technical workstream. No handoffs. No gaps when the timeline compresses.

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  • Full FDD workstream management and Big 4 interface 
  • NWC peg negotiation and working capital defense 
  • SALT exposure quantification and indemnification negotiation 
  • Disclosure schedule preparation: drafted in-house, coordinated with outside counsel 
  • HR and employment diligence workstream ownership 
  • Contract and vendor diligence response 
  • Closing waterfall build and stakeholder reconciliation 
  • Post-close transition support (90–120 days) 

Strategic Advisory

For companies that have the seat filled - but want access to operator-level transaction experience.

Some companies have a CFO, a controller, or a strong VP Finance - and still need access to someone who has been through three exits, negotiated a NWC peg, prepared disclosure schedules, and sat across from a Big 4 diligence team. Strategic advisory engagements provide that access without a full embedded engagement.

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  • Board meeting preparation and investor communication
  • Transaction readiness assessment - what will a process actually require
  • Capital raise strategy and financial narrative review
  • SALT, revenue recognition, and compliance guidance
  • Management team coaching for diligence and buyer presentations
  • Second opinion on deal terms, LOI review, and closing mechanics


This is not day-to-day support. It’s targeted access at the moments that matter.

A Selective Posture

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Engagements are selective. Sierra works with a small number of companies at a time - growth-stage founders and leadership teams building toward an eventual raise or exit, and VC/PE investors who need an operator, not an advisor, supporting their portfolio. The work is designed to be additive - alongside existing teams or as the primary operational executive across accounting, finance, HR, legal, and compliance. Engagements are structured for depth, not volume.

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For Venture Capital & PE Investors

Most portfolio companies don’t have one person who owns finance, HR, legal, and compliance from the

For VC and PE firms, Sierra provides two distinct services: embedded CFOO coverage for portfolio companies at any stage, and an operator’s diligence perspective on potential investments. 


In each of her three acquisitions, Sierra was brought in to improve business outcomes - rebuilding pricing architectures, restructuring cost bases, designing organizations, drafting and negotiating contracts, leading compliance initiatives, and co-developing the narrative that acquirers bought. Then she owned the transaction: 209 diligence items personally managed, representing 65-80% of the total workload.
 

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 someone who can assess, align, and build - not just report. As a single operator, Sierra owns accounting, finance, HR, legal, and compliance. Fewer advisors in the room. Full accountability for outcomes. This is operating partner work - embedded inside companies, not delivered from the outside.


  • Portfolio company CFOO coverage (Seed → Exit)
  • Value creation planning across revenue, efficiency, and risk levers 
  • Organizational assessment: team, structure, compensation alignment 
  • Revenue model diagnostic: pricing architecture, unit economics, customer quality  
  • Operator diligence lens on acquisition targets
  • Pre-investment financial and operational assessment
  • Exit readiness evaluation across the portfolio 

By Stage - The Right Support at Every Level

Pre-Revenue / Seed

The decisions you make now are the ones that get scrutinized at Series A - and again at exit.

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.

  

▸  Entity structure: choose correctly, it’s expensive to change later 

▸ Financial model & projections for seed raise

▸ Accounting foundation: chart of accounts, close process & bookkeeping oversight

▸  Revenue recognition methodology: set it now, not when a buyer asks

▸  Cap table, equity compensation strategy, and 83(b) elections

▸  IP assignment agreements for every founder, employee, and contractor  

▸  Employment agreements: drafted, signed, and filed from day one  

▸ Cash flow management & burn analysis

Series A

This is the sweet spot for strategic acquisitions. The infrastructure you build now is what a buyer scrutinizes - or what they have to rebuild after close.

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.


▸  ARR methodology formally defined, documented, and defensible

▸ Pricing strategy review: ACV optimization, packaging, discount governance

▸ Cohort analysis and customer cube: retention by vintage, expansion revenue

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

▸ Board reporting package & updates: investor-grade

▸ Revenue recognition & GAAP compliance (ASC 606)

▸ SALT nexus analysis: you’ve been selling into multiple states since day one 

▸ Organizational design and first finance hire criteria

▸ Employment documentation audit: offers, proprietary rights, contractor agreements

▸ SOC II Type 1 initiated with your technical team

▸ Capital raise preparation: financial model, narrative, data room

Series B+

 All three levers matter equally. The company is scaling and the operational infrastructure must keep pace. 

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.


▸ Unit economics documented and defensible: Rule of 40 trajectory visible

▸ Net revenue retention tracked monthly: the metric buyers scrutinize first   

▸  Department-level budgeting and variance analysis 

▸ Multi-entity consolidation and international reporting

▸ ERP implementation or migration to enterprise-grade system  

▸  Operational alignment between departments: shared KPIs  

 ▸ Contract management: standardized terms, renegotiation where needed 

 ▸ Compensation architecture: retention and management incentive design  

▸ SOC II Type 2 completed or in progress

▸ SALT compliance current: VDAs filed where exposure exists

▸ Data room skeleton built and maintained as an operating tool  

▸ Management team assessed for transaction readiness 

Exit Preparation

The base is built. The multiple is what’s left to optimize - and the ROI on preparation is 10-17x.

A private SaaS company at $5M ARR trades anywhere from 3x to 6x revenue in the current market - a spread of $15M to $30M on the same base. The difference between those numbers is determined almost entirely by the risk profile: the quality of the finance function, the compliance posture, the documentation, and the team. The cost of the preparation work that moves a company from the low end to the high end of that range is $300-500K. There is no other investment with a higher ROI at this stage. 


▸  Business diagnostic: revenue quality, cost structure, compliance posture, team readiness

▸ Revenue model assessment: pricing defensibility, customer concentration, cohort analysis 

▸ Organizational assessment: who stays, who transitions, retention and carveout design 

▸ CIP narrative co-development with business leaders and bankers

▸ Contract book review and standardization: terms, MFN exposure, termination clauses 

▸ SALT exposure quantified and remediated before a buyer quantifies it for you
▸  Revenue recognition reviewed against ASC 606: adjustments made before a buyer’s team makes them
▸  IP chain complete: every assignment documented  
▸ AI readiness and defensibility documented
▸  CIP narrative co-developed with leadership and bankers

▸ Data room built substantially complete before LOI

▸ Management team prepared for FDD sessions and buyer presentations

▸ Full transaction execution through close: FDD, NWC peg, disclosure schedules, closing waterfall 

▸ Post-close transition support and integration continuity 

Sierra Hinson, CMA · Founder & CFOO

  Sierra Hinson operates as an embedded enterprise operator - owning the systems that determine enterprise value and executing transactions through close. She has spent 19 years embedding inside growth-stage technology companies - owning the full operational infrastructure that determines enterprise value. Three strategic acquisitions as the operating executive: Curiosity.com to Discovery Communications, Signal Digital to TransUnion, and KnowledgeHound to YouGov. In each company, she was brought in to improve business outcomes and chart the path to exit.

  That work went far beyond finance. She rebuilt pricing architectures that changed how companies sold. She took $20M out of a cost structure by restructuring teams, renegotiating vendors, and refactoring technology infrastructure with engineering. She designed organizations, cascaded OKRs from the boardroom to every department, and structured retention programs that kept the right people through transactions. She drafted and negotiated contracts directly - client agreements, vendor terms, and a cross-border stock purchase agreement - engaging outside counsel for specialized matters. She led cross-functional GDPR compliance. She managed finance, HR, tax, payroll, and compliance across 17 countries as direct ownership, not oversight. She terminated employees in Japan during an active transaction. She co-developed the CIP narratives that acquirers bought - building the strategic story over years, not weeks.

  Then, when each process started, she owned it: 209 diligence items personally managed across accounting, finance, legal, HR, compliance, and IP - representing 65-80% of the total workload. NWC peg negotiation. SALT analysis. Disclosure schedules drafted in-house. Closing waterfall. 83 items closed in the peak week - while the business kept running.

 Her career spans childcare marketplaces to customer intelligence platforms - Sittercity, Signal Digital, Curiosity.com, KnowledgeHound, Pear, Globalli, and more than a dozen others across SaaS, adtech, media, marketplace, and global HCM. She serves as Expert in Residence at 1871 Chicago and is a Limited Partner at Service Provider Capital.

 Sierra works alongside existing leadership teams - bringing the operational and transaction scope that most finance functions don’t have. The work is designed to be additive: alongside your CFO, your controller, or your founder-led finance function, not in place of it.

Increasingly,  Sierra's work extends to the investor side - providing acquisition target assessment and transformation advisory for VC firms and PE sponsors evaluating and supporting growth-stage companies. It's the natural evolution: three exits from the operator seat - with full accountability for accounting, 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 hope to work with her again!"


President, Sittercity

Let’s have a direct conversation about your enterprise value

 Whether you’re a founder who needs someone to own the operational infrastructure your company has outgrown, a leadership team preparing for a raise or a transaction, an investor who needs an operator’s lens on a target, or a banker or attorney with a client who isn’t ready yet - most engagements start the same way: a direct conversation about where enterprise value is being created and where it’s leaking.

LET'S TALK

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