Selected deals / Commercial history
The hard part
is rarely the feature.
It’s the incumbent. The budget. The migration risk. The people who need confidence before they can commit.
Selected enterprise work, with client identities anonymized. Dates indicate the role period unless a specific duration is stated.
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Learning Management Systems
Higher Education · EdTech · System access
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Regulated assessment
$10M+ territory · 50+ accounts
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Cybersecurity SaaS
State, Local, and Education pipeline
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Independent advisory
Business systems & automation
01 / The evidence
Different constraints.
Specific decisions.
Open a story for the situation, the approach, and the result. Contract value, annual value, pipeline, and account longevity are labeled separately.
8 of 8 selected stories
Cybersecurity SaaS / SLED
Build a territory
from a blank map.
$2.5M+PIPELINE
An unmapped Western US territory. A public-sector buying process
involving security, risk, legal, and procurement.
from a blank map.
The constraint
Develop a new State, Local, and Education (SLED) territory during a period of post-investment restructuring.
The decision
Build national public-sector channel relationships, engage the full buying committee, and co-author business cases around security, total cost of ownership, and legacy displacement.
The outcome
Generated $2.5M+ in pipeline in under 12 months, including $1.2M+ qualified in the first two quarters. Multiple RFPs reached final negotiation before a company-wide reduction in force. These are pipeline figures, not booked revenue.
Regulated assessment / Institutional
Solve the annual budget.
Win the decade.
$2.0MTOTAL CONTRACT VALUE
A constrained institutional budget became the starting point for a
ten-year remote-invigilation agreement.
Win the decade.
The constraint
A key regulated account needed an annual price it could sustain. A conventional contract structure would not resolve the budget constraint.
The decision
Negotiate an aggressive annual price in return for a ten-year commitment. Align engineering, product, compliance, and institutional stakeholders through hands-on proof-of-concept work.
The outcome
Signed a $2.0M total-contract-value agreement with ten years of contractual longevity and competitive lockout. This sat within a $10M+ western territory spanning 50+ regulated institutions and public-sector accounts.
Learning Management Systems / Private university
Replace the platform.
Earn the trust.
$1.5MTCV / $500K ACV
A homegrown Learning Management System, an entrenched incumbent, and a
six-month RFP requiring institutional confidence at every level.
Earn the trust.
The constraint
Displace a highly customized system built over decades while managing strong incumbent advantages and close financial scrutiny.
The decision
Lead a six-month evaluation, a full-day demonstration for 50 stakeholders, and direct CEO-to-VP alignment. Connect platform standardization and student-retention visibility to institutional priorities.
The outcome
Closed a three-year agreement at $500K annual contract value and $1.5M total contract value. Displaced the legacy platform and created referral momentum into affiliated institutions.
Learning Management Systems / Public university system
One approval.
A path for every campus.
System-widePROCUREMENT ACCESS
Individual campus opportunities faced the same repeated security,
legal, compliance, and pricing reviews.
A path for every campus.
The constraint
Campus-by-campus sales cycles were duplicating the governance work required to make a purchase.
The decision
Move the evaluation to central procurement and system leadership. Make the case for administrative efficiency, pre-vetted terms, and a repeatable purchasing path.
The outcome
Won placement on the approved master procurement vehicle. Downstream campuses could buy without restarting duplicative security, legal, compliance, and custom-pricing reviews.
Learning Management Systems / Online university
Make migration
a manageable risk.
$1.0MTOTAL CONTRACT VALUE
A fast-growing private online university needed to replace its
homegrown engine without disrupting learning.
a manageable risk.
The constraint
The CIO, security teams, and academic leadership had concerns about sensitive data, course migration, faculty adoption, and delivery continuity.
The decision
Work through security, privacy, architecture, and migration concerns over several months. Demonstrate the content-import engine to establish course consistency and reduce faculty adoption risk.
The outcome
Closed a $1.0M total-contract-value agreement and supported the migration of the academic portfolio without course-delivery disruption.
Learning Management Systems / Global organization
Learning at scale.
A global responsibility.
GlobalTRAINING DELIVERY
An international faith-based organization needed availability,
localization, scale, and continuity across its training environment.
A global responsibility.
The constraint
Support a centralized learning environment across a large international footprint, with demanding continuity requirements.
The decision
Use established institutional trust to reach central decision-makers, then coordinate technical validation around resilience, scale, and localization.
The outcome
Won the global enterprise training contract. The delivery architecture was subsequently adopted for additional high-stakes global training programs.
Learning Management Systems / Private university
Win the account.
Build for the long term.
12+ yearsACCOUNT LIFECYCLE
Persistent outbound work became a nine-month evaluation and an account
that remained referenceable for more than twelve years.
Build for the long term.
The constraint
Create an opportunity at a major private university, then earn confidence through an extended institutional evaluation.
The decision
Combine persistent cold outreach with on-site alignment at a national higher-education conference. Lead the evaluation and pilot over nine months.
The outcome
The account remained active, referenceable, and revenue-generating more than twelve years after the original pursuit. This describes the resulting account lifecycle, not continuous personal account ownership.
Learning Management Systems / Online university
Make governance
the business case.
ComplianceDRIVEN REPLACEMENT
A fragmented homegrown environment was failing to provide the
visibility needed for accreditation and academic governance.
the business case.
The constraint
Replace a learning system during a period of serious accreditation and reporting pressure.
The decision
Work with academic leadership to connect data visibility and workflow consistency to compliance reporting. Reframe the evaluation around governance and risk mitigation.
The outcome
Advanced the homegrown-system replacement and modernized delivery infrastructure during a critical review period. No contract value or exact close date is published for this case.
ACV = annual contract value. TCV = total contract value. Pipeline is not booked revenue. The $500K ACV and $1.5M TCV figures refer to the same LMS agreement. Role chronology includes a family caregiving break in 2019–2023; see the full resume.
02 / What carries across the work
Find the constraint.
Build the path through it.
Map the decision.
Work with the buying committee, not just the initial sponsor. Understand who owns risk, budget, adoption, and approval.
Resolve the real uncertainty.
Bring architecture, security, and migration questions into the evaluation early, with the right engineering and product counterparts.
Structure a workable agreement.
Connect the solution to institutional priorities, procurement requirements, and commercial terms the buyer can support.
The work continues