A mission-driven leader who builds — highly effective teams, durable strategy, and organizations ready for what's next. Through StillDayOne.ai, I partner with nonprofits and the technology companies that serve them — helping ISVs build a go-to-market that actually lands in the sector, and helping nonprofits get the culture and AI readiness to put that technology to work.
Leslee Stockton has spent her career positioning herself at the cutting edge of technology — from early-stage startups in virtual and augmented reality, AI, and machine learning, to roles at Microsoft (Xbox) and Amazon Web Services.
Over six-plus years at AWS, she built the company's Charities Enterprise space into a global team, growing AWS's nonprofit and social-impact business from $1M to $130M in annual revenue. She partnered with many of the world's largest and most trusted mission-driven organizations — National Geographic, the American Red Cross, NPR, PBS, the Associated Press, Save the Children, CARE, and countless more — alongside the technology partners and ISVs building solutions for them. The heart of that work was always the same: helping customers translate sophisticated technology into real outcomes for the communities they serve.
That commitment runs deeper than her day job. Leslee sits on the advisory board of Imua Onipāʻa, a Maui-based nonprofit building career pathways for Hawaiʻi residents through training, mentorship, and support in high-demand industries. She has served on nonprofit boards, led nonprofit organizations, and remains an avid volunteer in her community — because the work of serving others isn't something she advises on from a distance. She lives it.
Today, through StillDayOne.ai, she works both sides of the table: helping nonprofit technology companies build and execute their go-to-market in the sector — strategy, target accounts, relationship-led pipeline, and co-sell partnerships — and advising nonprofits on a culture of innovation and AI readiness. The work of innovating never really finishes. It's a mindset, not a milestone.
Helping leadership teams understand that innovation has no finish line — and building the curiosity, structure, and habits that keep it continuous rather than episodic.
The organizations accelerating with AI are the ones that start with their customer and work backwards — building on a foundation of sound security and infrastructure. I help leaders get that foundation right first, so the technology serves the mission instead of getting in the way.
For technology companies serving nonprofits: a GTM strategy built for how the sector actually buys — prioritized target accounts, relationship-led pipeline from a deep network, and co-sell motions with complementary partners, handed off as playbooks your team can run.
Worked closely with nonprofits on Maui to put technology to work in support of relief and recovery efforts.
Helped nonprofit partners adapt operations and service delivery through one of the sector's most disruptive periods.
Supported organizations like NPR and PBS navigating recent funding disruptions under DOGE and USAID.
A confident, evidence-based look at what separates the organizations pulling ahead with AI from those stuck at the starting line — and what the people who serve Hawai'i's residents can do today to build for what's coming. Followed by a panel on the pitfalls of AI with Eugene Chang (IEEE/MIT).
Why innovation is a continuous mindset, not a one-time initiative — and how to build it into a team.
The unglamorous infrastructure and security work that determines who accelerates with AI and who stalls.
Moving past the layoff reflex toward reinvestment in the durable skills that actually compound.
With shelter leaders, national partners, and government officials working to end homelessness among women, children, youth, and families — under this year's theme, Safe Shelters Save Lives.
August 2026Three days with 350+ United Way leaders, board members, and staff from across the western U.S., centered on resilience, collaboration, and innovation in serving communities through complex times.
At the Hawai'i symposium, I was asked where organizations should begin with AI. Here's the shortlist I trust — practical, mostly free, and chosen for the people who serve their communities every day. Start with one, finish it, and use it in your actual work. That's how readiness gets built.
Free, ready-to-teach cloud and Generative AI Foundations curriculum for higher-ed institutions, with faculty access and hands-on learner labs.
No-cost, self-paced cloud and AI training with shareable digital badges. Open to anyone, no technical background required.
Foundational generative-AI program using PartyRock and Bedrock, aligned to the AWS AI Practitioner certification. No prior experience needed.
A no-charge, cohort-based, faculty-facilitated option for higher ed, government, nonprofit, and workforce-development programs.
Self-paced courses on working effectively with AI for everyday use, with verifiable certificates. No paywall, no coding.
The classic non-technical primer on how to think about and work with AI strategically. Clear, practical, no code.
Interactive, hands-on introduction to what AI is, how it works, and how to use it — free to start.
AI contact center with real-time agent assist, call summaries, and self-service. Anthology uses it to handle student financial-aid and enrollment questions 24/7, freeing staff for the human moments.
Open-source benefits screening (built on Anthropic) covering 40+ benefits in minutes. 100,000+ households helped, $52M+ in benefits accessed across six states.
Statewide Data Exchange Framework: secure, real-time sharing of health and social-services data across counties and agencies. "Goodbye fax machine."
AWS's foundational guide on how procurement teams can enable responsible AI adoption while meeting compliance requirements. The best first read.
Buy through existing contract vehicles and cooperative agreements (OMNIA Partners, NASPO), with flexible pricing and FedRAMP filtering. Includes Claude for Education.
A generative-AI tool that guides procurement staff through writing comprehensive RFP scopes — with a human in the loop, even on unfamiliar topics.
The 16 principles Amazon uses every day to discuss new ideas and make decisions — from Customer Obsession and Invent and Simplify to Bias for Action.
How Amazon puts Day 1 into practice: customer obsession, two-pizza teams, one-way vs. two-way door decisions, and a real appetite for experimentation.
The original "What does Day 2 look like?" letter — a short read on resisting proxies, embracing external trends, and high-velocity decision-making.
AWS's public-sector take on the four pillars — culture, mechanisms like Working Backwards, architecture, and small autonomous teams.
A resource guide to the Culture of Innovation program: PR/FAQs, distributed decision-making, and workshops for teams ready to go deeper.
Colin Bryar and Bill Carr's insider account of the mechanisms behind Amazon's culture — the PR/FAQ, the six-page narrative, and single-threaded leadership.
Strategic advisory across cloud, capital, and nonprofits — with a focus on reducing homelessness through better data.
Trusted contact-center and customer-experience intelligence, built for total visibility across every channel.
Grant management built for nonprofits — streamlining grant tracking, compliance, and restricted-fund allocation without disrupting your existing general ledger.
If you're working through big challenges in data, AI, cloud, or nonprofit digital transformation, I'd love to connect.
Leslee@StillDayOne.ai