Engagement Manager · Post-sale delivery · AI-fluent

Engagement
Portfolio

Not a project manager. Not an account exec. The connective tissue between delivery reality and customer expectation — fluent in both languages simultaneously.

Two altitudes at the same time: VP-level conversation with a sponsor one day, rolling up sleeves with solution architects the next. Range is the requirement. Two engagements below: JPMorgan Chase via Oracle (Tier-1 strategic, 95%+ SLA on 130+ Service Requests) and Akamai’s InfoSec portfolio (Integrated Account Team across four concurrent programs, 30–50 stakeholders). The approach, six artifacts I ship every cycle, and the numbers pulled from real Service Value Reviews.

The Approach

The EM is the single source of truth.

Product, engineering, sales, and the customer sit at different levels of context on any given Tuesday. My job is to hold all four at the same level — so leadership stops chasing updates and starts making decisions. The dashboard is a decision-making tool, not a reporting tool.

Phase 01
Discover

Executive intake, IAT map, and mutual success criteria ratified. The real question isn’t what tasks — it’s what the sponsor wants to have achieved in 3–6 months outside of day-to-day deliverables.

Phase 02
Design

Charter, RAID, and Customer Account Review published within 30 days. Steerco monthly, IAT weekly, escalation paths documented. Governance layer that works whether the SOW is fully defined or still forming.

Phase 03
Deliver

Weekly exec status. Signal over noise. Trusted advisor to sponsors, coach to the TPM and SA. Fingers in everything, but not driving all of it — that’s the difference between an EM and a bottleneck.

Phase 04
Sustain

Hypercare, operational maturity, and expansion-signal detection. I identify expansion; sales closes it. Every engagement produces a closing brief the account team can turn into a save or an expansion motion.

Featured Engagements

Two signature engagements, both post-sale.

Real customers, real numbers — sourced from my own Service Value Reviews and Customer Account Reviews. Every fact below is a signal an EM interviewer can probe.

The Artifacts

Ten working documents that hold an engagement together.

Not templates. The actual shape of what I write and iterate on every week. Anonymized where legal requires it; numbers are illustrative on the sample below.

Scenario — anonymized enterprise engagement. An illustrative program charter I would take to sponsor sign-off in the first 30 days of an engagement. Fortune 500 financial services client, cloud CRM migration, $4.2M budget, 18-month program, 5,000 end users.

Section 1 — Program Overview
Enterprise Cloud CRM Migration
Business Case

Legacy CRM costs $2.8M/year in maintenance with 67% user satisfaction. Cloud migration reduces TCO by 40%, moves user satisfaction to 85%+, and enables AI-powered analytics unavailable on the legacy platform. ROI breakeven at month 14.

Scope
  • Migrate 12M+ customer records across three business units
  • Integrate with 8 downstream systems (ERP, billing, support)
  • Custom workflow automation for SOX / GLBA compliance
  • Train 5,000 end users across 14 office locations
Success Criteria
  • 100% data migration with zero data loss
  • 85%+ user adoption within 90 days of go-live
  • < 2% increase in support tickets during transition
  • All compliance requirements maintained through cutover
Constraints & Assumptions
  • No production downtime during peak trading hours (9am–4pm ET)
  • Regulatory freeze window: Nov 15–Jan 15 (no deployments)
  • Vendor provides dedicated migration engineering team
  • 15% budget contingency ($630K) held for risk mitigation
Section 2 — Governance & Stakeholders
Program Organization
Executive Sponsors
  • CTO — Final go/no-go authority
  • COO — Business readiness sign-off
  • CISO — Security & compliance approval
Steering Committee
  • Head of Sales Operations
  • Head of Customer Support
  • Head of Data & Analytics
  • Vendor Program Director
Working Team
  • Program Lead (me)
  • 2 Technical Architects (client + vendor)
  • 4 workstream leads: Data, Integration, Change, Compliance
  • Migration engineering pod (12 engineers)
Cadence
  • Steerco — Monthly, 90 min, executive decision forum
  • Working team — Weekly, 60 min, tactical alignment
  • Exec status — Weekly written, distributed Monday 8am
  • Escalation SLA — 24h for Sev-1, 3d for Sev-2

Customer Account Review — the primary EM artifact. Six-to-eight-month strategic roadmap per account, tied to what the sponsor wants to have achieved outside of day-to-day deliverables. Presented at the annual on-site briefing and refreshed at every QBR.

Customer Account Review — sample structure
Six-month strategic roadmap · Enterprise account
01 · Where the customer is going

Two paragraphs on the sponsor’s business priorities for the next 18 months — sourced from board decks, earnings calls, and direct conversation. Not restated at every meeting; owned as the frame everything else fits into.

02 · Operational maturity today

Where the account sits on the maturity curve for each product module. Utilization, adoption depth, self-service ratio. The “is this account okay” question, answerable in one glance.

03 · The six-month plan

Three commitments the IAT will deliver against — each tied to a business outcome, not a feature. Owner, due date, and the leading indicator that says it’s working.

04 · Expansion signal (not ask)

What’s emerging that could become an expansion motion. Cleaned signal for the AE: adjacencies the customer is talking about, budget cycles, competing initiatives. EM identifies, sales closes.

05 · Risk register — account-level

Not project risks. Account risks: sponsor turnover, competing initiatives, budget pressure, integration debt. Each with an early-warning indicator, not just a mitigation.

06 · What we’re asking of the customer

Every roadmap has a shared-responsibility layer. Their power users, their exec sponsor attendance, their compliance sign-offs. Written down so nobody discovers it in month five.

RAID = Risks, Assumptions, Issues, Dependencies. The single tracker every steerco pulls from. Kept short, kept current, always tied to an owner and a next-review date.

Live RAID — sample entries, sample week
Type ID Description Owner Status Next Review
Risk R-014 Third-party integration vendor missed Sprint 8 commitment; puts UAT date at risk if not resolved within 10 business days. M. Ortega, VP Eng Open Wk 19 Steerco
Issue I-022 Data validation script rejecting 3.2% of legacy records due to schema mismatch. Vendor patch requested; workaround in place. S. Patel, Data Lead In progress Wk 18 Working Team
Assumption A-008 Assumes client’s internal ticketing system stays on current version through Q4. Client roadmap review confirmed 07/09. R. Chen, Head of Product Validated —
Dependency D-031 Compliance sign-off on GLBA data handling required before Prod cutover. Legal review scheduled 07/22; not yet complete. J. Rivera, CISO Open Wk 20 Steerco
Risk R-015 Sales Ops team bandwidth limited during Q4 quota push; UAT participation may slip, extending cutover window. Head of Sales Ops Mitigating Wk 19 Steerco

Weekly Executive Status Report, Week 18. One page. Signal over noise. Sent Monday 8am so sponsors read it before their first meeting.

Executive Status — Program Phoenix, Week 18
Overall Health
Amber
Schedule
+3d
Budget
$1.9M / $4.2M
Scope Change
0 items
What changed this week
  • Sprint 8 vendor slip surfaced Wednesday; mitigation plan agreed within 24h
  • Compliance sign-off (GLBA) rescheduled from 07/15 to 07/22
  • UAT enrollment: 87% of the 40-person pilot cohort confirmed
What needs a decision
  • Accept 3-day slip on UAT start, OR reduce Sprint 8 scope by 2 features. Recommend Option A.
  • Add $28K vendor spend for data-enrichment tooling? ROI break-even 90 days.
What I’m watching
  • Sales Ops UAT bandwidth during Q4 quota push
  • Vendor Sprint 9 planning — leading indicator of Sprint 10 risk
  • Change management: town hall attendance dropped from 320 to 240
What’s next
  • Legal review of GLBA handling — scheduled 07/22
  • UAT kickoff — 07/29 (moved from 07/26)
  • Steerco — 08/05, 90 min, decisions above will be tabled

Risk Register. Every risk has an owner, a probability, an impact, and a mitigation. Reviewed weekly at working team, escalated monthly at steerco.

Top open risks — ranked
# Risk Probability Impact Category Mitigation Owner
1 Vendor Sprint 8 slip cascades to Sprint 9 and 10, pushing UAT start beyond Q3 close. High High Vendor Delivery Reduce Sprint 8 scope by 2 non-critical features; commit to Sprint 9 planning by Fri. M. Ortega
2 GLBA compliance sign-off delayed pending Legal review; blocks Prod cutover. Medium High Compliance Legal review calendared 07/22; escalation path to General Counsel documented. J. Rivera
3 Sales Ops UAT participation drops during Q4 quota push; extends validation window. High Medium Business Readiness Secondary UAT cohort identified from Support Ops; can flex in if primary slips. Head of Sales Ops
4 Change management fatigue: town hall attendance down 25% over 3 weeks. Medium Medium Change Management Shift to 15-min bi-weekly “office hours” format; managers cascade key messages. Comms Lead
5 Data quality on 3.2% of legacy records blocks clean migration; vendor patch requested. Medium Low Data Workaround in place; vendor ETA on patch 08/01. Manual reconciliation as fallback. S. Patel

Program Timeline. 18-month view, shown at every steerco. The stripe marks “you are here.” Critical path in tobacco; parallel streams in brass and sage.

Program Timeline — 18 months, Weeks 1–72
M1
M2
M3
M4
M5
M6
M7
M8
M9
M10
M11
M12
M13
M14
M15
M16
M17
M18
Discovery & charter
Architecture & design
Data migration build
Integration build
Compliance & audit
Change mgmt & training
UAT — you are here
Cutover & go-live
Hypercare & closeout

Statement of Work — the contract inside the contract. Signed by client sponsor before any billable hour hits the engagement. Locks scope, deliverables, acceptance criteria, and change process. Ambiguity here is where enterprise engagements go to die.

Statement of Work — Enterprise Engagement
SOW · Fortune 500 Cloud Migration · Q3 2026
01 · Scope Statement

End-to-end migration of legacy CRM to cloud platform across three business units. Includes data migration, integration of 8 downstream systems, workflow automation, and end-user training. Excludes hardware procurement and any non-CRM system modifications.

02 · Deliverables (In Scope)
  • Migration plan & playbook (Week 4)
  • Data mapping specification (Week 8)
  • Integration architecture doc (Week 12)
  • Training curriculum & certification (Week 40)
  • Go-live cutover plan (Week 60)
  • Hypercare runbook (Week 66)
03 · Out of Scope
  • Hardware refresh at endpoints
  • Non-CRM legacy system decommissioning
  • Third-party vendor negotiation
  • Marketing communications strategy
  • Any custom development past 5% of build
04 · Acceptance Criteria
  • 100% data migration with zero data loss (validated)
  • 85%+ user adoption within 90 days of go-live
  • < 2% increase in support tickets during transition
  • All compliance requirements maintained through cutover
  • Sponsor sign-off on hypercare exit criteria
Milestone Schedule & Payment Terms
Payment tied to acceptance, not effort.
ID Milestone Target Date Acceptance Criterion Payment %
M-01 Discovery & Charter Approval Week 4 Signed program charter; steerco confirmed 15%
M-02 Design Phase Sign-Off Week 12 Architecture & data-mapping specs approved by CTO 20%
M-03 Pilot Cohort Live Week 28 50-user pilot cohort operational; adoption >80% 15%
M-04 UAT Complete Week 56 UAT sign-off; zero critical defects open 20%
M-05 Production Go-Live Week 60 Successful cutover; 100% data migrated 20%
M-06 Hypercare Exit Week 68 85%+ adoption; ticket volume normalized 10%
Assumptions · Change Control · Exit
Assumptions
  • Client provides dedicated technical liaison for duration
  • Access to legacy CRM data granted within Week 2
  • Client-side change management team resources available
  • Executive sponsor available at monthly steerco
Change Control Process
  • All scope changes submitted as written Change Requests
  • Impact assessment within 5 business days
  • Steerco approval for changes >$50K or >2 week impact
  • Approved changes updated in RAID within 24h
Exit / Termination
  • Either party may terminate for material breach with 30-day cure
  • Payment for accepted milestones due at exit
  • Knowledge transfer runbook required within 15 days
  • IP transfer per Master Services Agreement

Sprint plan, backlog, and Scrum artifacts. Two-week cadence with a small dedicated delivery pod. The EM does not run standups — the Scrum Master does — but the EM owns sprint-level commitments to the client sponsor and the Sprint Review agenda.

Sprint 18 — Goal & Commitment
“Ship Data Mapping V2 & validate against three business-unit test cohorts.”

Sprint dates: Jul 15 – Jul 26. Team capacity: 68 points (baseline). Sprint commitment: 62 points. Confidence: 78% (High). Scope reduction from Sprint 17 velocity slip carried forward as stretch.

Sprint Backlog — committed stories
ID Story Points Owner Status
S-042 Data mapping schema V2 — consolidate 8 downstream integrations into unified schema 13 M. Ortega (Data Lead) In Progress
S-043 Migration script for legacy Salesforce records (400K records) 8 S. Patel In Progress
S-044 Business Unit 1 test cohort validation (100 records) 5 R. Chen Done
S-045 Business Unit 2 test cohort validation (100 records) 5 R. Chen In Progress
S-046 Business Unit 3 test cohort validation (100 records) 5 R. Chen Blocked
S-047 Rollback runbook for BU3 (if validation fails) 8 J. Rivera Ready for Review
S-048 Sprint 18 review deck for client sponsor 3 I. Wheeler (EM) In Progress
S-049 Compliance narrative update (audit prep) 5 J. Rivera Ready for Review
S-050 Stretch: refactor error logging pipeline 10 M. Ortega Stretch
Velocity — last 6 sprints
Averaging 62 points · trending up · target 65 by Sprint 20
48
Sp 13
55
Sp 14
51
Sp 15
64
Sp 16
58
Sp 17
62
Sp 18
Actual velocity Below target (slip) Current sprint (committed)
Ceremony calendar — two-week cadence
Monday · Week 1
Sprint Planning
4 hours. Team commits to sprint goal + backlog. EM confirms alignment to steerco commitments.
Daily · 9am
Daily Standup
15 minutes. Scrum Master runs. EM attends 2x/week to surface exec risk signals.
Wednesday · Week 2
Backlog Refinement
90 minutes. Groom next 2 sprints of stories, estimate, split epics.
Friday · Week 2
Sprint Review
60 minutes. Client sponsor + steerco invited. Demo, feedback, roadmap alignment.
Friday · Week 2
Sprint Retrospective
75 minutes. Team-only. What worked, what didn't, one improvement to try.
Definition of Done — team-wide
  • Code reviewed by at least one peer engineer
  • Unit tests written & passing; coverage ≥ 80%
  • Integration tests passing on staging environment
  • Product Owner acceptance criteria explicitly verified
  • Documentation updated (README, API docs, runbook)
  • Deployed to staging and validated against test data
  • Security review completed for any auth-touching code
  • Accessibility (WCAG 2.1 AA) verified for UI changes
  • Rollback plan documented for production-touching changes

Engagement lifecycle flow. The map I draw on the whiteboard in the kickoff meeting so the whole team knows what happens when, who owns it, and where the feedback loops are. Any moment on this diagram, I can point to what I'm doing and what's next.

Engagement Lifecycle — end-to-end flow
From Signed SOW to Renewal · 18-month view
Signed SOW Weeks 1—2 Discovery Week 3 Kickoff & Charter Weeks 4—12 Design & Plan Gate Ready? no — iterate yes 2-week cadence Sprint N Plan · Build · Review next sprint Gate UAT pass? no Week 60 Go-Live Weeks 61—68 Hypercare Renewal Motion learnings → next SOW
Gate criteria — where the flow makes decisions
Gate 01 · Design Ready?

Architecture approved by CTO, data mapping validated, integration contracts signed. If no, iterate design with focused unblock session — do not enter sprint mode with ambiguous requirements.

Gate 02 · UAT Pass?

Zero critical defects. Sponsor-designated business users sign off. If no, return to sprint mode for targeted defect resolution — do not schedule cutover under pressure.

Feedback Loop · Renewal → Next SOW

Every closing brief becomes input to the next engagement's SOW. What we’d do differently, what the client wants next, where the roadmap lands. Loop is terracotta dashed: not part of the linear flow, but critical to portfolio growth.

RACI Matrix — who does what. Signed at Kickoff. Reviewed quarterly. Ambiguous ownership is the single biggest source of missed dates in enterprise engagements — this matrix is what I point at when someone says “I thought you owned that.”

Engagement RACI — deliverables × stakeholders
Signed at Kickoff · Reviewed at every Steerco
Deliverable Sponsor EM (me) TPM SA Legal Account Exec Finance
Program Charter A R C C I I I
Customer Account Review C R C I — I —
RAID Log I R C C — I —
Executive Status A R C I — I I
Risk Register C R C C C I C
Sprint Planning — C R C — — —
SOW & Change Requests A R C C C C A
Compliance Sign-Off A C I C R — —
Renewal Motion C R I I I A C
Value Realization Report A R C I — C C
RResponsible — does the work AAccountable — single point of accountability CConsulted — input before decision IInformed — kept in the loop
The rules I enforce
One Accountable per row

Never two “A”s. If two people are accountable, no one is. The exception on this matrix is SOW & Change Requests — because Legal and Sponsor share accountability for different aspects (contract vs. business).

The EM is Responsible on most rows

Not because the EM does all the work — because someone has to be responsible for making sure it happens. If nobody's R in the matrix, the deliverable slips.

“—” is a decision, not an oversight

Every empty cell was discussed at kickoff. If Sponsor doesn't need to be Consulted on Sprint Planning, the matrix says so explicitly — not by omission.

Re-signed at every quarterly review

Roles change, people leave, stakeholders shift. RACI is a living document. Anyone can request a change — but the change goes through the same Change Request process as the SOW.

Correspondence

Now running post-sale engagements at Coupa.

These artifacts landed me the Sr. Principal Engagement Manager role at Coupa — AI & agentic solution delivery for enterprise customers, where the SOW isn’t fully defined (that’s the point). The portfolio stays up as a reference for fellow EMs and anyone building their own.

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