Jon OlsonCarmel, IN · ET
Product Leadership · Enterprise SaaS |⁠ Platforms |⁠ AI

Commercial rigor.AI leverage.Portfolio scale.

Fifteen years turning product strategy into revenue. I ran a $100M+ ARR SaaS division through an on-prem to multi-tenant cloud transformation, and today lead a company-wide identity platform spanning 200+ products. Alongside that, I build the AI tooling and practices that make product teams faster.

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Jon Olson
Jon Olson · Business & Technology Leadership
Track record — by the numbers2011 — PresentSheet 01
01 · Portfolio owned$100M+ ARRPublic safety SaaS division, four years
02 · R&D directed$20M+ / yrInvestment priorities across 10 business units
03 · Cloud cohort10× growth2022 → 2025, revenue per customer 1.5–2×
04 · Org built25+ PMsInside a 200-person cross-functional team

02 · Selected work


Tyler Technologies

Identity platform for 200+ products

Strategy and rollout of one workforce and citizen identity layer across the whole portfolio — on an architecture that cuts 90% of the prior model’s cost, with savings models product leaders use to prioritize.

Platform · Identity · 2026 → present

Public Safety Division

On-prem to multi-tenant SaaS

Led the cloud transformation for mission-critical emergency-response software (CAD, responder mobile and records): 10× cloud cohort growth and 1.5–2× revenue per customer, with client-segmentation tooling I built to pick and evaluate candidates.

Cloud transformation · CJIS · GovRAMP · 2022 → 2025

Next-generation product

Field reporting, rebuilt

Redesigned and launched a multi-tenant field reporting product on a fully automated CI/CD pipeline with team-owned DevOps and AI capabilities — 90% less implementation effort and better win rates.

0 → 1 · Multi-tenant · AI

WorkForce Software

A $6M commercial reset

Restructured hardware commercial strategy on a $10–15M line: ~$6M in added annual revenue guarantees, ~$1M in vendor savings, 25% sales lift — alongside launching the WorkForce Suite experience.

Pricing & packaging · Platform UX

03 · About


I started out building pricing models for $200M in deal opportunities, and automated my own job down from days to thirty seconds. That instinct never left: I run product the same way — find the leverage, build the tool, hand it to everyone else.

Since then I’ve been a hands-on integration lead, a platform product director, and the head of product for a nine-figure division. I care about commercial discipline and product operations rigor in equal measure — scorecards and capital allocation on one side, a 100+ member customer advisory board and structured discovery on the other.

I also founded and lead Tyler’s company-wide AI in Product Management community of practice, and build internal AI tooling used by dozens of teams. Texas A&M BBA, Information & Operations Management.

Roles
Product Lead, Identity PlatformTyler Technologies · 2026 → present
Director, Head of Product ManagementTyler Technologies, Public Safety · 2021 → 2025
Director of Product ManagementWorkForce Software · 2017 → 2021
Product Owner, Integration Design LeadBenefitfocus · 2013 → 2017
What I lead
Product strategy & visionPlatform & identity productsAPI & integration platformsMulti-tenant cloud architecturePricing & packagingProduct operationsPortfolio health & scorecardsCross-functional leadershipAI in product managementRegulated & security-sensitive software

04 · Contact

Let’s talk
shop.

Always up for a conversation about platform strategy, product operations, or what works at portfolio scale. There’s also a voice agent in the corner that knows my background — ask it anything.