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Outsourced CFO Services: What Founder-Led Businesses Need to Know

Outsourced CFO Services: What Founder-Led Businesses Need to Know

August 24, 2026/in Insights/by Amy Chamberlain

Most founder-led businesses build their finance function in whatever order the business needs, moment in time. Someone gets hired to handle the books first, then payroll, then eventually a controller once transaction volume outgrows what the existing systems can handle.

Nobody plans for the point where the business needs a financial leader, not just processing. That is why outsourced CFO support for founder-led businesses have become a common bridge, especially for companies preparing for a raise, sale, or simply outgrowing the systems they’ve relied on to this point.

Why founders delay bringing in finance leadership

Hiring a full-time CFO is a significant commitment, in cost and in fit, and most founders wait until the need is undeniable before starting that search. In the meantime, financial planning tends to live in the founder’s head, in handoff spreadsheets, or in whatever existing hire can manage on top of their regular workload.

That approach works fine to a point. It stops working the moment someone asks for a real forecast, the board wants monthly reporting, or the business needs to understand its unit economics well enough to make a pricing or hiring decision with confidence.

There is also a cost of waiting. Every month a founder spends personally holding the financial picture together is a month not spent on product, sales or whatever else continues to grow the business. As well as whatever is currently in place getting further in the weeds – making it even more difficult to clean up down the road. That opportunity cost rarely shows up on a spreadsheet, which is part of why it’s so easy to defer.

What makes founder-led businesses different

A lot of financial advice is written for companies with an established team already in place. Founder-led businesses usually don’t have that starting point. The founder often is the finance function, at least in the sense of making calls that matter, even without the title.

That changes what outsources support actually needs to deliver: translating financial complexity into something a founder without a finance background can act on quickly, since most founders didn’t start the business to become a financial analyst.

What outsourced CFO support covers

An outsourced CFO engagement typically covers:

  • Cash flow forecasting built around the business’s actual runway and burn, not generic template
  • Board and investor reporting that answers the questions they actually ask
  • KPI tracking tied to the metrics that matter for the specific business model
  • Scenario planning for hiring decisions, pricing changes, or potential raise
  • Preparing the finance function for diligence, whether that’s an investor round or an eventual sale

This work sits on top of what’s already happening day to day, adding planning and analysis that most founder-led businesses never had the bandwidth to build themselves.

Signs it’s time

A few signals tend to show up before founders make the call: an inability to answer basic runway questions without pulling numbers together manually, board or investor requests that take days to fulfill, cash flow surprises that shouldn’t be surprises, and a founder spending hours each month on financial tasks that pull them away from running the business.

Individually, any one of these might feel manageable. Together, they usually mean the finance function has outgrown what the current setup can support, whether or not anyone has said so out loud yet.

Why timing matters more than most founders expect

The businesses that bring in outsource CFO support early tend to have more options later. They can choose the timing of a raise instead of being forced into one by cash crunch, and they can walk into diligence with reporting already in the place instead of building it under pressure.

Waiting until the need is obvious usually means building this infrastructure at the worst possible moment, with a deadline attached and less room to get it right. The businesses that wait are rarely worse off because they waited for a specific number of months. They’re worse off because the choice about when to build it stopped being theirs to make.

What to expect from an engagement

A good outsource CFO relationship starts with an honest assessment: what exists today, what’s missing, and what the business actually needs over the next 12 to 18 months. From there, the work usually moves through a few phases: getting the numbers reliable and consistent, building the forecasting and reporting the business needs, and then maintaining a steady cadence once that infrastructure is in place.

The pace of that work should match the business, not a fixed template. A business 6 months from a raise needs a faster build than one that’s simply outgrowing informal processes with no immediate deadline attached.

It should also come with a clear handoff plan. A strong, outsourced CFO relationship documents its wok well enough that if the company eventually hires someone full-time, that person isn’t starting from zero.

Common pitfalls when bringing in outside finance support

A few mistakes come up often enough to be worth naming directly. Founders sometimes wait until a raise, or sale is already in motion to start building financial infrastructure, which turns a planning project into a rush job with no room for error.

Others bring in outside support without giving that partner real visibility into the business, treating it as a reporting function rather than a planning one. The forecasting only gets as good as the context behind it, and a partner working from incomplete information can’t catch problems before they surface.

Another being choosing a partner based on cost alone, without checking whether they’ve actually worked with businesses at a similar stage. A partner used to supporting much larger companies may build something more complex than a founder-led business can maintain once the engagement ends.

A realistic scenario

Consider a founder running a services business doing several million dollars in revenue, with a small team handling day-to-day finance and no dedicated forecasting. An investor conversation surfaces the need for a 3-year model and monthly reporting the founder has never had to produce before.

Building that from scratch, while also running the business, usually isn’t realistic on the founder’s own timeline. An outsourced CFO can build the model, set up the reporting cadence, and get the business investor-ready in weeks rather than months, without requiring a full-time hire the business isn’t read to support yet.

6 weeks later, the founder walked into the investor meeting with a forecast and reporting package that held up under real questions, instead of trying to explain gaps in the numbers on the spot.

How to evaluate a fit

Not every outsource CFO offering looks the same worth asking; does this partner have direct experience with founder-lead businesses at a similar stage or mostly larger more established companies? Can they show examples of reporting in forecasting they felt elsewhere? What’s the plan when the business eventually needs a full-time hire?

It’s also worth knowing how the partner communicates. A founder without a finance background needs someone who can explain a forecast in plain terms rather than handing over a polished model and expecting them to interpret it alone.

The bottom line

Outsource CFO support for founder lead businesses comes down to getting the financial leadership. A growing business needs it in the moment without waiting for the ideal time to make a full-time hire.

The founders who build this infrastructure early aren’t necessarily more financially sophisticated than the ones who wait they’ve just decided that financial readiness is worth building before a deadline forces the issue, which tends to be the difference between a razor sale process the good smoothly and one that doesn’t.

FAQs

Isn’t this just a different name for bookkeeping?

No. Day-to-day record-keeping handles what already happened. An outsource CFO focuses on what’s coming next; forecasting planning and helping the founder make decisions with real numbers instead of guesses.

How much does an outsource CFO cost compared to a full-time hire?

It depends on scope, but outsource support is almost always less than a full-time senior hire, since the business pays for the specific hours and expertise it needs rather than a full salary and benefits package.

At what size does a business actually need this?

There’s no fixed revenue threshold. The signal is usually the complexity of the decisions being made, a raise, a hiring plan, a pricing change, a sale or just outpacing what the founder or existing team can model with confidence.

What happens if we eventually hire a full-time CFO?

A good outsource CFO engagement documents their work clearly enough that a new hire can pick it up without starting over. Ask about this handoff process before starting the engagement. They can also most likely refer someone over who understands the process they already put in place. Making it an even smoother transition.

How do we know if the reporting we’re getting is good?

Good reporting answer is a real question without requiring a follow up meeting to explain it. If board members are investors, keep asking for clarification on the same numbers month after month the reporting isn’t doing its job yet regardless of how polished it my look.

https://www.chelseastreet.com/wp-content/uploads/2026/09/Blog-Outsourced-CFO-Services-What-Founder-Led-Businesses-Need-to-Know-1.png 630 1200 Amy Chamberlain https://www.chelseastreet.com/wp-content/uploads/2026/09/CSA_Long-Logo_White.svg Amy Chamberlain2026-08-24 14:50:282026-09-06 14:58:18Outsourced CFO Services: What Founder-Led Businesses Need to Know
Finance Integration Checklist for Post Acquisition

The Finance Integration Checklist After Acquisition That Actually Holds Up

August 10, 2026/in Insights/by Kenna Rooney

Most post-close integration checklists have a line for sales, a line for ops, a line for IT, and finance gets folded into “accounting cleanup,” even though it determines whether anyone trusts the numbers for the next 3 to 5 years.

That gap shows up fast. A finance integration checklist after acquisition determines whether the operating partner’s first board meeting is built on real numbers or best guesses.

Why finance integration gets treated as an afterthought

Sales and ops integration plans get built early because the stakes are visible: lose a customer relationship or a key operator, and everyone notices immediately. Finance integration problems are quieter. A misaligned chart of accounts or an unreconciled system doesn’t blow up in week one. It surfaces 2 or 3 months later, usually right when someone needs a clean number fast.

By then, the fix costs more than it would have on day one, because now there’s a backlog of transactions booked under the old structure that all need to be reclassified or reconciled retroactively. What would have been a decision in week one becomes a cleanup project in month three, and cleanup projects are always more expensive than the thing they’re cleaning up after.

There’s also a subtle reason finance gets deprioritized: it doesn’t have an obvious owner in most deal teams. Sales integration has a sales leader. Ops integration has an operator. Finance integration often falls to whoever happens to be closest to the books at the time, which usually means it gets handled reactively instead of planned deliberately. Reactive plans tend to address symptoms as they appear rather than the structural gaps causing them.

What a real finance integration checklist should cover

A finance integration checklist after acquisition needs to go well beyond “close the books on time.” At minimum, it should cover: 

  • Banking and treasury: opening new accounts, setting up treasury services, and mapping out how cash moves between entities during the transition.
  • Payroll and HR systems: reviewing the acquired company’s existing payroll configuration and identifying what needs to be reconfigured, especially where compensation classification differs.
  • Chart of accounts: assessing the current-state COA against what the combined entity actually needs, including dimension and segment design for reporting.
  • Accounting remediation: a detailed walkthrough of existing processes to catch revenue recognition issues, cash-to-accrual gaps, or other corrections before they compound.
  • FP&A and reporting: identifying data sources, standing up an initial KPI dashboard, and building toward a real forecast model rather than a static budget.
  • Opening balance sheet and closing statement: coordinating with valuation providers early, since accounting work has its own lead time and can’t be rushed at the end.

Skipping any one of these creates a gap that someone eventually has to explain to a board, a lender, or an LP.

These categories aren’t independent of each other. A payroll system reconfiguration affects the chart of accounts. A chart of accounts redesign affects what the FP&A team can actually report on. Treating each line item as a standalone task, rather than a set of interdependent decisions, is one of the more common ways integration checklists fall apart in practice.

A phased approach works better than a single deadline

Trying to complete finance integration all at once, by some arbitrary date, tends to produce rushed, undocumented work. A phased approach holds up better, and it maps reasonably well to how most acquisitions actually unfold operationally. 

In the first stretch after close, the priority is assessment and stabilization: getting banking and payroll functional, reviewing the existing chart of accounts, and identifying what data actually exists versus what still needs to be built. It’s unglamorous, foundational work, but skipping it means every later phase inherits the same gaps. This is also the window to reach out to valuation providers if an opening balance sheet needs to be prepared, since that work often has a longer lead time than teams expect. 

The next phase is where the real infrastructure gets built: the chart of accounts gets redesigned around the combined entity, an intercompany elimination framework goes in if there’s more than one entity involved, and the forecast model starts to take shape. This is usually the busiest phase, and it’s where having a dedicated owner for finance integration pays off most, since it involves more judgment calls than the stabilization phase did. 

The final phase is where reporting actually goes live: a first board package delivered, lender reporting running if applicable, and a documented month-end close process so the whole thing doesn’t depend on one person’s institutional knowledge. A good test for whether this phase is complete: could someone new to the finance team run the close process from the documentation alone, without pulling the person who built it into every step?

Common pitfalls

A few mistakes show up again and again in finance integrations: 

  • Treating the checklist as a one-time task instead of a phased plan with real ownership at each stage 
  • Waiting until month-end close breaks before addressing chart of accounts misalignment 
  • Starting ASC 805 valuation conversations too late, since these providers often need significant lead time 
  • Assuming the acquired company’s existing processes are “good enough” without a real walkthrough 
  • Building reporting for the business as it exists today instead of the combined entity it’s becoming 

Most of these pitfalls share a common root: treating finance integration as something that happens passively, alongside the “real” integration work in sales and ops, instead of as its own work stream with its own timeline and its own owner. 

How to assign ownership without overloading one person

One practical decision that’s easy to get wrong: who actually owns this checklist? In a lot of newly acquired companies, the answer defaults to whoever’s already doing the books, often a controller who’s also handling day-to-day close activity and doesn’t have the bandwidth to run a structured integration project on top of it. 

A better approach splits the work. Someone owns the overall plan and phase-by-phase milestones, while the categories themselves (banking, payroll, chart of accounts, and so on) get assigned to whoever has the most relevant expertise, whether that’s an internal hire, a fractional resource, or an outside specialist for something like ASC 805 valuation work. The goal is to make sure every task has a name attached to it and a date it’s due.

A realistic scenario

Consider a services business acquired as a platform’s second add-on. On paper, the acquisition made sense: complementary customer base, similar margin profile, an obvious cross-sell story. In practice, the acquired company’s chart of accounts had grown organically over a decade, with dozens of ad hoc expense categories that didn’t map to anything in the platform’s existing structure. 

Without a structured integration checklist, that mismatch might not surface until the first consolidated month-end close, when the finance team discovers that what looked like a straightforward roll-up actually requires manually reclassifying hundreds of transactions by hand, every single month, until someone rebuilds the chart of accounts properly. 

With a checklist in place from day one, that chart of accounts review happens in the first 30 days, as an assessment, not a fire drill, and the redesign happens deliberately in the following phase, before it’s had a chance to create months of manual workaround. The difference is whether that work happens on a schedule the team controls or one forced by a broken month-end close. 

Building your own checklist

The specifics of any finance integration checklist after acquisition will vary by deal. A services business integrates differently than a manufacturer, and a platform with several add-ons already in place has different needs than a first acquisition. But the categories above hold constant across most deals, and mapping owners and target dates against each one, phase by phase, is what turns a checklist from a wish list into something that actually gets executed. 

The firms that treat this as seriously as they treat sales and ops integration tend to hit their first board meeting with numbers they can stand behind. The ones that don’t usually find out the gap exists at the worst possible time: mid-diligence on the next deal, when the numbers need to hold up under scrutiny and don’t.

The bottom line 

A finance integration checklist after acquisition is the difference between a finance function ready to support the next deal and one still catching up on the last one. Building it early, phasing it deliberately, and assigning real ownership at each stage is what makes the difference between reporting that holds up and reporting that quietly falls apart the moment someone asks a hard question. 

None of this requires a massive team or an enterprise budget to get right. It requires treating finance integration as a real workstream from day one, with the same visibility and accountability given to sales and ops integration. It’s the function everyone else’s numbers ultimately depend on. 

FAQ

Do we need this if we already have a controller or an in-house finance team?

A controller running day-to-day close usually doesn’t have the bandwidth to also run a structured integration project on top of it. The checklist gives that team, or a fractional resource brought in alongside them, a plan with owners and dates instead of a list of things to get to eventually.

How long does a full finance integration usually take?

Most run 90 to 120 days from close to a documented, repeatable month-end close, though assessment and stabilization should start in the first 30 days regardless of company size. Deals with multiple entities or an opening balance sheet tend to run longer, mostly because of the valuation provider’s lead time, not the accounting work itself.

Does this apply outside PE-backed deals?

The categories hold for any acquisition, but the urgency changes. A PE-backed company answers to a board and often a banker, so a broken chart of accounts surfaces fast, usually in the first board package. A privately held acquirer without that reporting cadence can stretch the timeline, though the same backlog of unreconciled transactions still builds underneath it.

What happens if we just handle issues as they come up instead of following a checklist?

Skipped issues resurface later, and bigger. Fixing a misaligned chart of accounts in week one is a design decision. Fixing it in month four is a cleanup project with a backlog of transactions that need to be reclassified by hand. Reactive integration costs more, it just costs more later instead of now.

 

https://www.chelseastreet.com/wp-content/uploads/2026/08/Blog-Finance-Integration-Checklist-For-Post-Acquisition.png 630 1200 Kenna Rooney https://www.chelseastreet.com/wp-content/uploads/2026/09/CSA_Long-Logo_White.svg Kenna Rooney2026-08-10 20:28:262026-08-10 20:28:26The Finance Integration Checklist After Acquisition That Actually Holds Up

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Maheen Zubair Khan
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Maheen Zubair Khan

Associate

Maheen works across cash flow forecasting, financial reporting, and dashboard development at Chelsea Street, turning complex financial data into clear, actionable insights that support strategic decision-making for clients. Her unique combination of accounting expertise and technical skill gives her the ability to not just analyze the numbers, but build the tools that make them accessible.

Prior to Chelsea Street, Maheen served as a Financial Analyst in FP&A at Nexamp, where she supported forecasting, budget variance analysis, and built dynamic Power BI reports for executive leadership. She also brings experience from Indus Motors Company, where she automated reporting processes that reduced manual effort by 80% and replaced legacy systems with interactive dashboards.

Maheen is an ACCA Global Prizewinner in Taxation and is passionate about using automation and data visualization to eliminate manual processes — giving finance teams more time to focus on the analysis that actually moves the business forward.

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Charles Davis

Senior Associate

Charles works across audit, financial reporting, and client engagement initiatives at Chelsea Street, bringing a detail-oriented, process-driven approach to every engagement. His background in public accounting gives him a deep understanding of the financial infrastructure that PE-backed companies need to scale with confidence.

Prior to Chelsea Street, Charles spent five years at BerryDunn, where he led audit engagements across healthcare, financial services, and nonprofit clients — managing everything from planning through financial statement delivery. He served as the primary point of contact for clients and internal leadership alike, building the kind of cross-functional relationships that make complex engagements run smoothly.

Charles holds a Master of Science in Accounting and a Bachelor of Science in Accounting and Finance from the University of New Hampshire, with a CPA currently in progress.

He is passionate about improving processes and finding efficiencies that let teams spend less time in the weeds and more time delivering meaningful financial insight.

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Phil DiBuono

Managing Partner

Phil co-founded Chelsea Street Advisors to deliver a hands-on, execution-focused model that supports private equity portfolio companies beyond diligence and into meaningful finance and accounting transformation. A finance leader with deep expertise in private equity-backed companies, SaaS businesses, and M&A transactions, he advises B2B SaaS companies through periods of growth, integration, and value creation.

Prior to Chelsea Street, Phil served as CFO for Intentsify, a PE-backed B2B company in the marketing technology space, where he led complex financial operations, revenue recognition strategy, and integration across multiple acquisitions. Before Intentsify, he was a Partner at RSM, where he built one of the firm’s largest M&A books, and spent the decade before that at Deloitte working in the Boston, New York and London Offices.

Phil holds a BS in Accounting from Providence College and an MBA from the University of Connecticut. He is a Certified Public Accountant.

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Hannah Robinson

Director, M&A

Hannah Robinson, CPA, is a transaction advisory professional with over 10 years of experience in financial due diligence, assurance, and deal support for private equity sponsors, lenders, and corporate clients. As a Director at Chelsea Street, she leads quality of earnings and financial due diligence engagements as well as supporting purchase agreement negotiations and post-close disputes and reporting. Her experience spans buy-side and sell-side mandates across a range of industries, giving her broad perspective on deal risk, EBITDA quality, and working capital.

Prior to Chelsea Street, Hannah most recently served as a Vice President at Houlihan Lokey, where she led financial due diligence on 25+ middle-market transactions across software/SaaS, business services, fintech, insurance, and technology. She also has extensive cross-border experience from her time at PwC spanning the U.S., UK, Europe, and Australia on large-cap and middle-market transactions in retail, consumer, leisure, and technology.

Hannah is known for translating complex financial findings into clear, decision-relevant reporting for boards and investors, and for building tools and AI-enabled workflows that improve consistency and efficiency across engagements. She is a Certified Public Accountant licensed in Massachusetts and earned her Master of Accounting and Bachelor of Science in Management (Finance) from Tulane University’s A.B. Freeman School of Business.

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Emmanuel Gonzalez

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Emmanuel is an FP&A and controllership professional with experience spanning global enterprises including Hitachi Vantara, Pierre Fabre, Dr. Reddy’s Laboratories, and Nissan Motor. He specializes in financial modeling, budgeting, and forecasting, with a sharp focus on keeping execution aligned to Annual Operating Plans.

Across these roles, he’s built a track record of scaling financial operations through automation — standardizing reporting workflows and leading system implementations across SAP, Oracle, Anaplan, and tools like SQL and VBA to cut manual reporting cycles and strengthen data integrity across global sites.

Emmanuel has also served as a cross-functional business partner to operating departments and executive teams, managing high-volume O2C and P2P cycles and translating complex variance analysis into actionable OpEx and CapEx insights. He rounds out his finance toolkit with advanced proficiency in modern data environments like BigQuery, Snowflake, and Looker Studio, alongside hands-on ERP implementation experience.

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Kenna leads marketing at Chelsea Street Advisors.

She brings a finance and operations mindset to everything she does, understanding that the functions Chelsea Street supports are the backbone of every business. That perspective also shapes how she thinks about partnerships. Not as transactions, but as long-term investments in people and companies that want to build something together.

Prior to Chelsea Street, Kenna built her career in B2B demand generation with a focus on all things digital. She learned firsthand that the best results come from teams that are aligned, willing to work hard, and thinking about what comes next, not just what’s in front of them.

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Amy Chamberlain

Co-Founder and Managing Partner

Amy co-founded the firm to deliver a hands-on, execution-focused model that supports private equity portfolio companies beyond diligence and into meaningful finance and accounting transformation. She partners with investors and management teams to strengthen financial visibility, build scalable finance operations, and maximize enterprise value from acquisition through exit.

A finance leader with experience across corporate finance, M&A, and audit, Amy advises middle-market businesses through complex transactions and transition periods — helping them move from deal close to operational clarity with confidence.

Prior to launching Chelsea Street, Amy served as VP of FP&A at a private equity-backed, high-growth company, where she oversaw forecasting, financial reporting, and strategic finance initiatives. Previously, she spent over a decade at RSM, where she rose to Director of Transaction Advisory Services, developing deep expertise in financial due diligence across middle-market M&A. 

Amy holds an MBA from Suffolk University and is a Certified Public Accountant in Massachusetts. 

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Billy works primarily on forecasting, budgeting, and board reporting initiatives, partnering closely with leadership teams to deliver clear financial insights that drive strategic decisions. His experience spans both corporate finance and transaction advisory, giving him a well-rounded perspective on growth, performance, and operational scalability.

Prior to Chelsea Street, Billy most recently served as Manager of FP&A at Nexamp, where he supported executive leadership, owned company-wide forecasting, and built FP&A infrastructure from the ground up.

He also has extensive experience in M&A transaction advisory from his time spent at RSM and KPMG, performing buy- and sell-side diligence, including quality of earnings analyses for mid-sized and large service and commercial businesses.

Billy is passionate about leveraging innovation and automation to make finance functions more efficient—freeing teams to focus less on manual processes and more on meaningful analysis.

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Renee works primarily on reporting, revenue accounting, and operational finance initiatives, partnering closely with leadership teams to deliver accurate, timely insights to directly support decision-making. With experience spanning both public and private industries, she provides a well-rounded perspective on technical compliance, process improvement, and scalable finance operations.

Prior to Chelsea Street, Renee most recently served as Accounting Manager at Living Proof Inc, where she oversaw the full revenue-to-cash cycle, supported a two-day month-end close, and partnered with the Controller, CFO, FP&A, and marketing leadership on budget-to-actual analysis and spend management.

In addition, she holds extensive experience from her time at RSM US LLP, where she advanced to Assurance Supervisor, led multiple audit engagements for mid-market consumer and industrial goods companies, and supported considerations for M&A transactions.

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Emily Carroll

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Emily Carroll, CPA, is a seasoned accounting leader with extensive experience in controllership, financial operations, and scalable infrastructure design. As a Director at Chelsea Street Advisors, she delivers strategic controllership solutions to growing organizations and partners with executive leadership to build scalable finance organizations.

Throughout her career, Emily has built and led high-performing accounting organizations, including as a controller in industry. Her leadership philosophy centers on establishing clear accounting frameworks to build finance functions that support long-term, sustainable growth

Emily’s earlier Big 4 experience sharpened her expertise in transaction advisory, financial reporting, audit compliance, and technical accounting implementation, positioning her as an experienced advisor during periods of transformation and scale.

A Certified Public Accountant licensed in Massachusetts, Emily holds a B.S. in Accounting and Operations Management from Boston College’s Carroll School of Management