1
Senior Director, AI Transformation
Amplify
Remote
📍 Fully remote · HQ Brooklyn, NY
$190K–210K · posted
Leads company-wide AI transformation — where and how AI reshapes products and internal ways of working.
Strengths
Senior-director AI transformation is squarely your lane, and your AARP AI-adoption program is a close analog for a mission-driven, content-heavy organization.
Gaps
Verified requirements: Bachelor's in "business, computer science, information technology, or a related field" (your M.A. covers the related-field escape) and "demonstrated consulting experience" — engagement-leading, not billable, so stretchable. Plus K-12 curriculum and school-year cadence you'd be learning.K-12 education-technology company (curriculum and assessment software). · ~1,500–2,000 employees
2
Director, Internal and CEO Communications
Upwork
Remote
📍 Fully remote · HQ Palo Alto, CA
$163K–274K · posted
Owns internal communications for a fully distributed workforce and serves as the CEO's communications advisor and speechwriter, leading a small team and running all-hands.
Strengths
Internal comms, executive comms, all-hands and a distributed workforce is a near-literal restatement of your background — and the posting explicitly wants AI used in the drafting workflow.
Gaps
DELISTED BUT LIVE — re-checked 2026-08-18: the posting page itself is healthy (HTTP 200, full description, working application form, band still shown), but this role no longer appears on Upwork's own public Greenhouse board (6 postings listed, none of them this one). That usually means they have stopped sourcing for it. Confirm they are still accepting before you spend time on it. Beyond that: reports to a VP of Communications rather than owning the top comms seat, the operating rhythm is fast and informal, and Upwork hires in only 21 states — confirm DC or MD is on the list before applying.Publicly traded online work marketplace connecting businesses with independent professionals. · ~1,000 employees
3
Director, Strategic Initiatives - Legal AI
Thomson Reuters
Remote★ drivable
📍 Washington, DC (1 of 7 listed locations)
$137,200–$254,800 · posted
Turns Thomson Reuters' stated ambition of a $1B legal-AI business by July 2028 into charters, roadmaps and decision points — building the program operating system (governance, forums, cadence, decision rights, risk escalation) and mobilising Product, Engineering, Sales, Marketing, Customer Success, Data, Finance and Legal around it.
Strengths
The required list reads like your operating-model thesis written by someone else: "Build program operating systems including governance, forums, team cadence, decision rights, and risk escalation", "Develop executive communications, business cases, and decision briefs highlighting tradeoffs", and "Partner on change management and capability building for sustainable adoption". Washington, DC is a confirmed location on the requisition, so this one is drive-able. No JD, bar admission or attorney experience is required or even mentioned — "Legal AI" names the product line (CoCounsel, Westlaw), not the candidate.
Gaps
Every impact clause in the posting is commercial — "delivering measurable commercial, customer, product, or operational impact" and "commercial impact assessment" — and you have no revenue-side ownership. Legal technology, SaaS and the Salesforce/Gainsight/Gong stack are all named under Preferred and all new to you. The work model is unsettled: the Workday remoteType field reads "Remote", but the posting's only flexibility language is "work from anywhere for up to 8 weeks per year", which reads office-anchored. Confirm with the recruiter before assuming remote.Professional-information and software company — Westlaw, Practical Law, CoCounsel, Checkpoint and Reuters News, serving legal, tax, accounting, risk and government customers. · ~26,000–27,000 employees
4
Director, AI Strategy & Transformation
ButterflyMX
Remote
📍 Fully remote · HQ New York, NY
$200K–300K · posted
Leads AI strategy and transformation at a fast-growing smart building access control company.
Strengths
AI Strategy and Transformation is the primary lane. Fully remote, a growing company where you'd set direction rather than inherit a legacy structure. JD verified: $200K–$300K base with no MBA/consulting hard blockers.
Gaps
ButterflyMX is smaller and VC-backed — equity-heavy comp and VC uncertainty are real factors. Smart building / proptech is a new domain. Budget management experience expected.Cloud-based video intercom and smart access control platform for multifamily residential and commercial buildings. · ~300–500 employees
5
Director, AI Enablement
HealthEquity
Remote
📍 Fully remote · HQ Draper, UT
no range in the posting
Leads AI enablement and adoption across a health savings and benefits administration company.
Strengths
'Director, AI Enablement' is squarely the target title and lane. HealthEquity is mission-adjacent to AARP in healthcare administration — the AARP AI adoption program is a direct analogue. Digital enablement satisfies the 12+ years requirement.
Gaps
JD verified 2026-08-16: Non-Negotiable requirements include 'hands-on AI/ML experience in CX contexts (NLP, automation, predictive analytics)' and 'direct ownership of AI-driven CX decisioning systems.' A 'Not a Fit If' section flags backgrounds that emphasize 'governance coordination or execution of pre-defined initiatives' — which may describe portions of the AARP work. Read the full JD at the employer link before applying.Health savings accounts, FSA, HRA, and employee benefits administration platform. · ~3,000 employees