Assessed. Aligned. Built to Exit.

These are the systems that determine what a company is worth - and what it survives in diligence.

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) 

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 
• Vendor and contract management: terms standardization, renegotiation, cost review 
• 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 

Develop the Team 

Management team quality and depth is consistently one of the top three value drivers and risk factors in any institutional transaction. Buyers assess whether they are buying a business - or buying a founder. The work here is building a team that can survive scrutiny, execute through a transaction, and operate independently on the other side of it.

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• Organizational design: headcount planning, role definition, reporting lines, hiring repeatability  
• Compensation architecture: equity grants, 409a compliance, team incentive design 
• Leadership and succession: founder dependency, management depth, decision rights 
• International operations: multi-entity consolidation, transfer pricing, cross-border compliance
• Retention architecture: compensation benchmarking, transaction incentives, promotion criteria
• Operational alignment across departments: shared KPIs, shared language, financial fluency
• Management team assessment and preparation for FDD sessions and buyer presentations
• Culture and engagement: transition readiness, documentation of knowledge

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 

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) 

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.

 Three engagement models. One entry point..

Engagements are structured around where you are - not just where you're going. Whether you need someone to build the finance function, prepare for a raise, or own the full exit process through close, the engagement model follows the work. All three models begin with the diagnostic.

18+ months from a transaction · Internal finance capacity in place ________________________________________________________________________________________________________________

You have a capable team. What you don't have is someone who has been the operator accountable for 209 diligence items, a closing waterfall, and a business that still had to run while the process was happening. Advisory is a monthly working relationship - built around your diagnostic results, focused on the gaps that compound over time, and structured to make sure the decisions you're making now are the ones that hold up when scrutiny arrives.

Also the right model for founders at Series A or B who need a senior finance partner without a full-time hire - and want to build the infrastructure correctly the first time.

Best for: Founders and CFOs building toward a transaction who want a trusted advisor with transaction execution experience - not just financial counsel.

12–24 months from a transaction · CFO/CFOO seat open or underserved 

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I come inside. Not as a reviewer. As an operator accountable for outcomes across all four value creation levers - revenue, efficiency, people, and risk. Finance function build. Compliance posture. Organizational readiness. CIP narrative co-development. And when the process starts, I stay through close: data room, diligence ownership, NWC peg, SALT, disclosure schedules, closing waterfall. One person accountable for all of it.

Best for: Companies without dedicated CFO/CFOO coverage, or where the finance function was built for speed and needs to be rebuilt for scrutiny.

 Flexible structure · Scoped to what the company actually needs 

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The most flexible model. Starts as advisory and deepens based on what the diagnostic reveals and how the timeline evolves. Can include sleeves-up engagements for specific high-stakes work - SALT remediation, NWC peg analysis, data room build, management team preparation. Or a close-only engagement: embedded for the 90–120 days from LOI through waterfall, so the business continues to operate while the transaction gets done.

Best for: Companies with internal capacity that need transaction execution support at specific inflection points - or founders who want to start with advisory and build from there.