Cheri Hewlett, CPA

Technology & innovation executive · People builder · Operator · CPA · Veteran

Progress belongs to the people willing to challenge what no longer works.

I built my career by questioning accepted answers, looking beyond the boundaries of my role, and refusing to let hierarchy, politics, or bureaucracy stand between a meaningful problem and a better solution.

Technology is moving faster than traditional organizations can respond. I help close that gap — modernizing systems, aligning people, and creating the conditions for ideas to move, decisions to be made, and impact to scale.

Cheri Hewlett on the main stage

Expertise becomes systems. Systems create impact. Impact happens through people.

Point of view

For thirty years the person who saw the problem and the person who could build the fix were two different people, and everything got lost in translation. That gap is closing. The new innovator is the domain expert who can build — and the constraint is no longer capability. It's judgment.

01

Innovation is choosing the right problem

Most companies are solving the wrong problems faster. AI didn't fix that — it accelerated it. The first question is never can we build this. It's whether this is the problem that deserves the next six months.

02

ROI is the problem solved, not the time saved

Time doesn't disappear; it gets reallocated. The real question is what caliber of quality the team operates at afterward. Not working less — operating differently, and smarter.

03

Trust is the real moat

Everyone asks whether AI can do the work. The better question is whether we can prove it did it right — the difference between a system people adopt and one they quietly work around.

04

How you treat people is the strategy

Organizations don't outperform because they obsess over customers. They outperform because they invest in the people serving them. As AI absorbs execution, that becomes more of the job, not less.

As AI takes on more of the what and the how, leadership becomes even more about the why and the who.
Quote card: as AI takes on more of the what and the how, leadership becomes even more about the why and the who

Experience

The reach

Every industry. Every scale.

Two decades in office-of-the-CFO technology — audit, advisory, and enterprise SaaS — across every industry, working with some of the largest and most complex organizations in the world. The last four years have been focused on AI-native architecture and orchestration — building the systems, not just directing them.

Every seat in the lifecycle

Advisor. Planner. Builder.

Customer success, solutions consulting, product and business transformation, platform strategy, building, release, and enablement — including ownership of a new product line from idea to scale. Betting a company's transformation on software means knowing exactly where plans meet reality.

The spine

Air Force. Big Four. Founder. Operator.

U.S. Air Force — mission first, people always. PwC and Deloitte. Founded a CPA firm serving real estate investors and small businesses, and ran a rental portfolio for a decade. Every chapter required learning something new from zero.

Beyond the day job

Community. Board Member.

Serving as an advocate for the LGBTQ+ community and a respected presence among women entrepreneurs and founders. Serving on the board of an organization providing resources to domestic violence victims.

CPA (VA) · M.S. Accounting, Liberty University · B.S. Accounting & Computer Science, University of Maryland · Veteran · Los Angeles, CA

Portfolio

Intelligent Product Enablement

Code ships → the content keeps up

Release readiness. When engineers ship a change, the help articles, release notes, training video and sales briefing it needs are written to match. Nothing goes out until a person approves it.

The problem

Organizations now ship technology faster than their customers can absorb it. Documentation, release notes and training arrive late and uneven, so customers are left to work out a product that has already moved on — and support absorbs the difference.

The value in solving it

Customers get timely, clear, high-quality guidance the moment a release lands, so they can actually adopt what was built. Release velocity stops outrunning the customer, and the field walks in prepared instead of catching up.

IPE
Release Readiness Code change → content
Synced Release 26.3
Code merged PR #2841

services/close/variance.ts

- threshold = 0.05

+ threshold = config.entityThreshold

+ requireApproval(amount > 250_000)

ui/close/VarianceRule.tsx

+ <ThresholdPerEntityField />

migrations/0412_entity_threshold.sql

+ alter table close_rules add column…

3 files · 2 user-facing changes detected
Help articlesupdated

Two articles rewritten and a new screenshot taken

Release notes · 26.3in review

"You can now set a limit per entity. Anything over $250k needs approval."

Training videorendering

A 4-minute how-to, recorded from the new screens

Briefing for the teamdrafted

What to say, what to expect, and which customers to tell

A person approves every piecenothing auto-publishes

Acquisition Integration Engine

Capability comparison · survivor calls · migration plan

For an acquisitive software company: compare capabilities across every acquired technology, flag which implementation survives and which retires, and build the migration plan that folds the acquisition into one unified platform.

The problem

Growth through acquisition is a sound strategy — but only if the acquired technology gets folded into the existing stack quickly. Miss that window and you accumulate an arsenal of disconnected parts that never turns into customer expansion.

The value in solving it

The acquisition becomes part of one platform instead of another product to maintain: the surviving capability chosen on evidence, duplicates retired on purpose, and the migration sequenced so the deal compounds into expansion rather than fragmenting the portfolio.

AIE
Portfolio unification 3 acquired products
Board view Sequence
Capability comparison — which implementation survives 38 capabilities compared
Capability Platform Northwind Meridian Alto Survivor
Consolidation engine 4.6 3.1 2.8 Platform
Intercompany matching 2.9 4.8 2.2 Northwind
Disclosure reporting 3.4 4.5 3.0 Meridian
Identity & access 4.7 2.4 2.6 2.1 Platform
Close task workflow 3.8 3.9 3.7 Flagged · too close
Migration plan · generated4 waves · 18 months
Wave 1Single identity directory · all four productsdone
Wave 2Northwind intercompany lifted into platformrunning
Wave 3Meridian disclosure module ported, Alto retiredplanned
Wave 4One close workflow · legacy UIs sunsetplanned
Sequenced by dependency, not by deal date

Duplicate functionality

7 modules

auto-flagged for retirement

Needs a human call

2

scores within tolerance

Entities on one platform

412

from four systems of record

Autonomous Implementor

Intake → process analysis → auto-configuration → ROI

It starts with the problem the customer is trying to solve. The engine maps that problem to the technology that solves it, analyzes their actual process, translates it into implementation data, writes the configuration files, configures the system to their requirements — and tracks the ROI they were promised the whole way.

The problem

Customers arrive with a specific problem, shaped by everything unique about their business. Translating that into the technology is done by hand, so implementations run long, the original problem gets lost in the build, and nobody can quantify the return they came for.

The value in solving it

Quicker time to value, traceable value, and an accountability system: the configuration reflects how this business actually works, every step ties back to the problem they came to solve, and the return is measured against the numbers they walked in with.

IMP
Implementation run Accounts payable · 14 sites
Agent running
1 · Intake ✓ 2 · Capability map ✓ 3 · Process analysis ✓ 4 · Auto-configure 5 · Verify 6 · ROI tracking

Intake — the problem to solve

"We process 40,000 supplier invoices a month across 14 sites. Half are keyed by hand, approvals sit in email, and we're paying late fees on invoices nobody could find."

→ Invoice capture → PO matching → Approval routing
Process analyzer → implementation data31 steps read
"Site manager signs over $25k"approval_tier: 25000
"Freight can be 5% over the PO"match_tolerance: 0.05
"Pay on the 15th and the 30th"payment_runs: [15, 30]
"Never pay a duplicate invoice"duplicate_block: hard
Configuration writtenapplied to tenant

ap_config.yaml

sites: 14 · approval_chains: 6

approval_tier: 25000

match_tolerance: 0.05

routing_rules: 142 · validated

ROI tracked against intake

Days to approve9 → 2
Keyed by hand50% → 4%
Late-payment fees$310k → $18k

Time to value

3 wks

from a 6-week baseline

Guards

Config reviewed by a humanbefore apply
Fail-closed authorityon
Self-closed steps0

Roadmap Prioritization Engine

Due diligence · prioritization · allocation

Which problem deserves the next six months. Candidates are scored on impact, strategic fit, feasibility and signal, weighted by confidence, then re-ranked as evidence arrives — the judgment call, made in the open.

The problem

What to build next gets decided emotionally, or on a half-baked case, rather than on what will actually drive value. The people building are usually a step removed from the problems they are solving — and from how customers use the collection of products together.

The value in solving it

The decision gets made on evidence: every candidate scored on the same dimensions, grounded in how customers actually use the portfolio, re-ranked as new signal arrives — and defensible enough to walk a board through.

RPE
Decision intelligence Q3 candidate set · 11 scored
score = (impact × fit × feasibility × signal) ÷ effort × conf.
Scoring comparison
Candidate Score Impact Feas. Conf. Decision
Close automation for multi-entity 9.4 4.8 4.1 92% Pursue
Source-system connector library 8.1 4.2 4.6 88% Pursue
AI variance narratives 7.6 3.9 4.4 71% Watch
Mobile approvals refresh 4.2 2.1 4.8 64% Defer

Re-ranked this week

3

Evidence items

47

Gate status

Cleared

Decided by

Human

Compliance Knowledge Base

Citable retrieval · provenance · re-verifiable

Atomic rules that carry their own citations. Ask a question, get the governing rule and the policy that overrides it — not a paraphrase. The same retrieval pattern runs the company, domain and industry corpora.

The problem

An AI answer nobody can trace back to a rule is unusable where being wrong is a reportable event — and company policy sits in people’s heads, not in the model.

The value in solving it

Every answer walks back to the standard and the internal policy it came from, so an expert who does not trust the model can still verify it and sign off.

CKB
Compliance knowledge base 4,180 atomic rules · 6 corpora
Index fresh
When does a lease modification require remeasurement?
Governing rules returned 3 of 3 cited
RULE-1142 · ASC 842-10-25-8exact

A modification is a separate contract when it grants an additional right of use not in the original terms and the price is commensurate with standalone value.

RULE-1147 · ASC 842-10-25-11exact

Otherwise the lessee remeasures the lease liability using a revised discount rate at the effective date of the modification.

POL-0308 · Internal lease policy v4company overlay

Remeasurements above $250k require controller sign-off before the entry posts.

Provenance

Every rule cites source100%
Answers without a citationrefused
Last corpus verification18h ago

Corpora

Company policy612
Domain · US GAAP / IFRS2,240
Industry844
Compliance & controls484

Multi-Dimensional Orchestrator

Registry routing · fail-closed authority · memory

The layer every other system runs on. Work arrives from any direction — a support case, a use case, a code change, a product area — and lands in the same governed path: classified, routed from a live registry, checked against authority before it can act, verified against evidence after.

The problem

Agents that can act without governance are a liability, work arrives from four different directions, and every new specialist means another rewrite.

The value in solving it

One governed path for all of it: routed from a live registry, fail-closed on authority, verified against evidence — and a new specialist is a config entry, not a project.

ORC
Orchestrator · live registry 35 agents · 16 teams
Nominal
Entry points — one path, four doorsall normalized to one envelope

By support case

"Invoice stuck in approval"

→ triage · 34 today

By use case

"Three-way match at 14 sites"

→ analysis · 9 open

By code

Merged diff · PR #2841

→ readiness · 118 diffs

By product

Payables · release 26.3

→ roadmap · 6 areas

Active now

21

Scheduled jobs

46

Escalated

2

Denied by authority

1

Request trace req_8f31c
routeEntered by support case → payables-triage12ms
authorityPayment release denied · read allowed4ms
memoryRecalled 6 prior decisions · 2 above threshold88ms
actThree tools invoked under governed contract1.4s
verifyStatus recomputed from evidence · claim matches210ms

Dimensions routed on

intent domain authority urgency memory depth

Escalation path

Triage L1clear
Analyst L22 open
Systems · governanceclear
Past SLA thresholdself-escalates

Evidence

Cheri Hewlett
The builder

Verified figures are a checked, versioned snapshot of the engineering record. The build rejects blank, zero, partial, or regressed totals, so the last known-good numbers stay visible. Attested figures are career facts no script can check.

claim source state
16,983 contributions in the last yearcontribution record · 89% commits, 11% pull requests ✓ verified 6,916 commits authored across the systems belowgit · excludes bot and merge commits ✓ verified 1,725 pull requests written, reviewed and mergedcode review record · merged pull requests ✓ verified 131 live services running in productiongit · edge functions ✓ verified 302 reusable capabilities catalogued and maintainedcapability registry · read, not typed ✓ verified 3 yrs consecutive triple-digit YoY growth on a platform line I builtcareer · not machine-checkable — attested 20 yrs leading enterprise software, most of it in the office of the CFOcareer · not machine-checkable — attested

Speaking & writing

Cheri Hewlett on the BeyondTheBlack main stage before a full audience

Signature talks

  • Innovation Is Choosing the Right Problem

    Most companies are solving the wrong problems faster. AI didn't fix that — it accelerated it.

  • Trust Is the Real Moat in AI

    Everyone's asking "can AI do this?" The better question: "can we prove it did it right?"

  • People First: The True Responsibility of Leadership

    Organizations outperform because they invest in the people serving the customer.

  • Built, Not Born: What Resilience Actually Requires

    Resilience isn't a personality trait. It's a practice.

  • The Chapters You Don't Put on Your Résumé

    Your most important career chapter is probably the one you're embarrassed to talk about.

Presentations

  • 2022—2026BeyondTheBlack
  • 2026Product Advisory Collective
  • 2024BlackLine Investor Day · New York
  • 2024SAP Sapphire · Barcelona
  • 2024LWT Summit · Leading Women in Technology

Articles

Recorded & featured

Let's connect around the work that matters.

Podcasts & media

Interviews, commentary, and stories on leadership, innovation, AI, finance, and the future of work.

Consulting & advisory

Strategy, systems, and transformation to modernize, simplify, and drive meaningful outcomes.

Network & community

Connection, mentorship, and shared learning with leaders, builders, and thinkers driving change.

Speaking & events

Keynotes, panels, and roundtables that challenge thinking and inspire action.

Subject-matter expert

Deep expertise in finance, accounting, product, technology, operations, leadership, and AI.

Builds & portfolio

Products, prototypes, and operating systems turning insight and expertise into scalable solutions.

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