A career built across the full lineage of software product work.
I started my career writing front-end code in 1998. Twenty-seven years later, I'm leading Tierso - an AI development, network orchestration, and full-stack engineering firm operating at enterprise scale. The path between those two points runs through every job I now lead other people in.
I've owned product at companies you've heard of (DayJet's 1,400-aircraft Eclipse 500 fleet, the $3M-saving Walmart Data Portal, BluePoint Data's SkyView ahead of its Pomeroy acquisition) and at companies I built myself - founder of PreAsk and FindLiveBait.com, where I raised the capital, formed the team, and ran engineering, sales, marketing, customer support, and infrastructure simultaneously.
I'm an award-winning product leader with a $15M+ lifetime revenue contribution across 60+ digital products in 13+ industries: aviation, IT solutions, automotive, ad-tech, enterprise search, cybersecurity, network orchestration, banking, exchange platforms, blockchain, and data management. I trained at Foster Technical Center, Champlain College, and graduated from Full Sail University in Winter Park, Florida - earning the institution's Perfect Attendance Award through its 14-month accelerated B.S. in Digital Media.
Ask anyone I've ever worked with and there's one common denominator: I do the job before I lead the job.
Eight stories from a 25-year span - outcome first.
Each project is annotated by the role lens Dylan owned, drawn from the same five-role lineage he hires across today: UX / UI · UI Developer · Product Strategist · Product Manager · Head of Product.
Founding an AI engineering firm at enterprise scale.
Head of ProductProduct StrategistCEO
Challenge
By 2024, the AI tooling landscape had shifted in a way most enterprises weren't ready for. LLM integration, RAG pipelines, intelligent agents, and SDN-based exchange infrastructure were each technically reachable - but assembling them into a system that performs at scale required a kind of cross-discipline talent most companies don't have on staff and don't want to hire permanently.
The market had a gap: organizations needed an embedded engineering department, not a vendor.
Approach
I founded Tierso to be exactly that - an embedded engineering firm built around three deeply interlocked competencies, with a single platform spine underneath:
AI development - custom LLM integrations, intelligent agents, RAG pipelines, and end-to-end automation workflows.
Full-stack engineering - React / Next.js platforms with SEO-grade performance, responsive design, and CMS integration.
One API gateway - every module of the platform sits behind a single, governed entry point. Enterprise clients get a coherent surface area rather than a constellation of services.
Operating-grade SLAs from day one - production accuracy is measured, not promised. The 99.2% AI-accuracy figure is observed, not aspirational.
Outcome
Tierso runs 2.4M AI requests per day at 99.2% accuracy. The exchange marketplace processes $4.2B in daily volume. The platform comprises 18 modules behind one API gateway, with 200+ years of combined team experience behind the bench. The tagline - Build Faster. Scale Smarter. Win Bigger. - is the operating discipline: every project we accept must measurably move at least one of those three vectors for the client.
The thesis is intact, the numbers are real, and the next chapter is in front of us. tierso.com →
Walmart Global Tech·Jan 2023 - Jan 2024·Senior Product Manager (Contract)
$3 million saved in the first six months.
Product ManagerProduct Strategist
Challenge
Walmart Global Tech brought me in to lead Product Managers and stabilize a struggling Walmart Data Portal (WDP) initiative. The system was sprawling, the cross-team coordination was fragmented, and the cost of running the existing data flows was hurting the business case before launch.
The mandate: make WDP shippable, performant, and quantifiably cheaper to operate.
Approach
Owned all UX/UI decisions for the cloud-based Walmart Data Portal - a single decision-maker accelerated a previously consensus-stalled program.
Led 12 Product Owners across the US and India - re-aligned each team around a quarterly OKR cadence and a shared backlog discipline in Jira.
Conducted Product Strategy with Walmart staff and stakeholders to identify priority items, OKRs, and the quarterly Roadmap.
Wrote Epics, User Stories, and bug tickets in Jira for development teams in two hemispheres - kept handoffs unambiguous and review cycles short.
Mobile React Native product strategy - set the technical direction and acceptance criteria for the mobile surface, where most of the cost-saving wins eventually landed.
Mentored junior Product Owners - invested in the bench so the program would keep performing past my contract.
Outcome
$3M in cost savings within the first six months of launching WDP - a measurable bottom-line result, not a theoretical one. The Product Owner organization went from "fragmented" to "coordinated." Junior PMs I mentored continued to ship after the contract closed. The mobile React Native strategy became the surface on which most ongoing efficiency gains were realized.
The Walmart engagement is the clearest answer to the question investors actually want answered: can this person operate at scale and deliver measurable savings?
LandTech Data Corporation·Sep 2017 - Mar 2021·Technical Product Owner
Cloud-rebuilt a regulated SaaS, end to end.
Product StrategistUX / UIProduct Manager
Challenge
LandTech's title-transfer software was a category leader on legacy infrastructure - and the legacy infrastructure was the constraint. A regulated industry demands precision in how data moves and who sees what; modernizing the software meant rebuilding it for the cloud while preserving the workflows real title-transfer professionals depend on every day.
Approach
Partnered with the Executive and Department teams to define Objectives and the Business Roadmap.
Led the team in redesigning Landtech's Title Transfer software and the internal customer-service CMS.
Identified Business Objectives for outlining the Product Lifecycle and Release Plan in Jira.
Transferred client needs and product knowledge to provide prototype solutions for both the Business and Development teams.
Developed an omnichannel User Experience redesign for the new SaaS, cloud-based Title Transfer Software - a regulated workflow rendered on the surfaces real users prefer.
Outcome
3.5 years of consistent ownership across a regulated rebuild is the case study by itself. Title transfer is unforgiving software: a UX mistake doesn't just hurt conversion, it damages a regulated transaction. Owning the lifecycle, in-house, for 3.5 years, with a clean rebuild on the way out - that's the proof point.
Avanquest (Contract)·Sep 2021 - Aug 2022·Senior Product Owner
Monetization at scale, run across four continents.
Product ManagerProduct Strategist
Challenge
Avanquest's monetization stack - H20, QuickLaunch, and Web Companion - runs at the intersection of installation software, lead generation, and white-label media-buyer relationships. The product surface was already mature; the challenge was orchestrating product ownership across teams in Canada, Europe, Ukraine, and India, while coordinating with outside Media Buyers on joint white-label projects.
Approach
Owned Avanquest's monetizing and installation software - H20, QuickLaunch, and Web Companion - across the full product lifecycle.
Led development efforts with multiple remote teams in Canada, Europe, and Asia.
Created Product Roadmaps, Quarterly Initiatives, Goals, and KPIs for QuickLaunch and the H20 product family.
Managed the Product Owner team responsible for H20 - including the Avanquest H20 Installer.
Partnered with outside Media Buyers on joint white-label projects, including localization-aware monetization design.
Ran grooming and Sprint Planning meetings reviewing Sprint Goals and engineering questions in Jira.
Oversaw UI and UX resources across Discovery, Design, Development, and QA phases.
Wrote User Stories and Bugs in Jira for overseas development teams in Ukraine and India.
Documented project information, campaign resources, and release plans in Confluence - kept the system observable for everyone, regardless of timezone.
Reviewed and monitored performance with Power BI integrated against Oracle - the analytical loop that made monetization tuning quantitative rather than narrative.
Outcome
Three live products coordinated cleanly across four continents for a year. The case study a recruiter or partner cares about here is operational maturity at distance - running a multi-product portfolio across timezones without losing engineering velocity or product clarity.
PreAsk (founder)·Jan 2014 - Aug 2017·Founder · Product Manager
Founded a company. Raised capital. Shipped a marketplace.
Head of ProductProduct ManagerProduct Strategist
Challenge
I founded PreAsk in 2014 to solve a specific class of problem: connecting a network of suppliers to a buying signal in real time. The first vertical we picked was live bait - an industry where the existing buying experience was friction-heavy, the suppliers were fragmented, and there was no software platform serving either side well. The bigger play was the platform itself: a Network Orchestration system that could be re-pointed at other verticals once we proved it.
Approach
Successfully raised capital for team formation and Agile development of the Network Orchestration Platform.
Constructed the Go-to-Market strategy, Product Roadmap, and Release Plans for FindLiveBait.com.
Launched FindLiveBait.com as a Web Application sitting on top of PreAsk's Network Orchestration platform.
Designed an omnichannel experience for FindLiveBait's online application, with AI/ML requirements baked in from the start.
Managed Engineering, Sales, Marketing, Customer Support, and Infrastructure teams simultaneously - the founder span no employed CEO ever has.
Set service pricing on Client Projects and Marketplace Service Agreements.
Conducted Stakeholder Interviews and Competitive Analysis of major US competitors for Gap Analysis.
Maintained client relations with all accounts on the PreAsk Platform - the relationships are what make a marketplace stick.
Backlog grooming, sprint planning, user stories, requirements, acceptance criteria, and bug logging in Jira.
Utilized Salesforce for research, journey mapping, and integration with Marketing and Sales workflows.
Outcome
PreAsk became my real-world graduate program in building a software business end-to-end. I've since returned briefly to PreAsk in 2022–2023 to deliver a Mobile Check Application for Okeechobee Steakhouse on top of the platform, demonstrating that the orchestration model still has legs across verticals.
For an investor, the through-line is simple: I've raised capital, formed a team, set pricing, owned the marketplace, and delivered a real product to real customers. The skills that matter at Tierso today were forged here.
TBC Corporation·Apr 2009 - Oct 2009·Information Architect
$3 million in revenue across two days.
UX / UIProduct Strategist
Challenge
TBC Corporation, headquartered in Juno Beach, FL, operates four distinct retail tire brands - Big O Tires, Tire Kingdom, NTB, and Merchants Tire - each with its own customer base, brand identity, and digital surface. The marketing organization needed a coordinated weekend email campaign that respected each brand's identity while driving conversion across the entire portfolio inside a tight window.
Approach
Designed and executed the weekend email campaign across all four TBC retail brands - Big O Tires, Tire Kingdom, NTB, and Merchants Tire.
Managed branding integrity across Big O, NTB, Merchants, and Tire Kingdom's interfaces so each campaign asset stayed on-brand for its retailer.
Translated client feedback and challenges into user stories in MS TFS for the Agile development team.
Produced personas, taxonomy, user stories, and wireframes from business requirements using Axure Pro.
Worked with the Google Analytics review team to establish metric points and increase conversion awareness across the campaign.
Developed solution prototypes for a new user experience across TBC's websites and POS system.
Outcome
The two-day weekend email campaign generated over $3 million in revenue across TBC's four-brand retail portfolio - $3 million dollars in 2 days.
BluePoint Data·Mar 2011 - Dec 2013·Product Owner & UX Strategist
Built SkyView ahead of BluePoint's Pomeroy acquisition.
Product ManagerProduct StrategistUX / UI
Challenge
BluePoint Data sold managed IT services into a market where most competitors looked identical on paper. The R&D team had a conceptual idea - what would become SkyView - for a monitoring and analytics product that could differentiate the offering. The challenge was getting from concept to a production-ready application that would survive enterprise scrutiny and shift the conversation with prospects.
Approach
Translated conceptual business ideas into rapid prototypes - wireframes and feature lists that the development team could actually build against.
Product owner across all three AI/ML products - maintained constant visibility on every project, ensured client feedback hit the development team in time, and kept quality consistent across releases.
Managed interface releases through the entire product lifecycle - from R&D handoff through QA and into clients' hands.
Conducted stakeholder interviews with senior staff and account managers at clients carrying $3M–$15M in annual income - these are the conversations that decide whether a managed-IT product gets renewed or replaced.
Performed competitive analysis and provided UX best-practice recommendations specific to the IT-services industry.
Produced research artifacts - gap analyses, taxonomies, flows, user stories, and persona definitions for the system's actual users.
Outcome
SkyView shipped, exceeded the service-level norms of incumbent managed-IT providers, and became part of BluePoint's differentiated offer. The company's overall product trajectory - including SkyView - helped position BluePoint Data for its acquisition by Pomeroy.
This case study is the longest answer to a simple question: can this person take a research idea, get it shipped, and contribute to an outcome a company eventually gets acquired for?
World Avenue · Kitara Media·Oct 2008 - Mar 2011·Senior UX Designer
Redesigned an online ad-platform from St. Thomas.
UX / UIUI Developer
Challenge
World Avenue's Kitara Media division ran an online ad-network platform whose existing GUI and user experience hadn't kept pace with the underlying capability. Ad placement is a workflow-heavy product, and the team needed redesigns that respected the operator's daily reality - fast - while also producing rapid prototypes for client-facing applications.
Approach
Led UX/UI Design on Kitara Media's online ad-network platform.
Redesigned the GUI and User Experience for the ad-placement product.
Wireframed and developed prototypes for clients' web-based applications.
Designed online media-placement application screens with localization-applied layouts.
Coded HTML5 pages and implemented CSS on a Java framework using Dreamweaver.
Produced branded Graphics Style Guides, Style Sheets, and Web Assets for the Agile development team.
Designed user-experience flows and displays for the ad-placement web application.
Developed system Personas, User Stories, and Scenarios for client social-networking systems.
Travelled 50% of every month to develop out of St. Thomas, USVI - running R&D in a different timezone built a discipline around documented handoffs that paid dividends in every later role.
Outcome
Two-and-a-half years of UX/UI ownership over an ad-network platform that depends on operator efficiency for its margins. The transferable skill: shipping clean front-end work that an Agile development team can build against, while running half the month from a different timezone. That discipline shows up in every remote-team engagement I've taken since.
DayJet Corp·May 2002 - May 2008·Creative Director & Front-End Engineer
Branded a 1,400-aircraft Eclipse 500 fleet.
UX / UIUI Developer
Challenge
DayJet was building an air-taxi service from scratch, on top of a brand-new aircraft platform - Eclipse Aviation's Eclipse 500. The founding team's order, signed jointly with Eclipse, Pontiac, and BMW, was 700 aircraft with an option for 700 more - 1,400 total - making it the largest non-military aviation order in world history at the time.
The internal mandate was massive: brand the entire fleet, design every customer-facing surface, build the reservations system, and stand up the dozen internal applications a from-scratch aviation operator needs.
Approach
Owned all branding efforts and User Experience projects across DayJet's Agile development teams - desktops, smartphones, kiosks, microsites, CMSs, and emergent AI/ML surfaces.
Designed and maintained DayJet's e-commerce reservations system on the .NET framework, plus 12 internal applications.
Travelled to LA, Albuquerque, and Pontiac, Michigan to collaborate on aircraft configuration with engineers from Eclipse, BMW, and Pontiac.
Configured seat leathers and cabin amenities with engineers in Pontiac for the Eclipse 500 fleet.
Worked through contract, budgetary, performance, and limitation specifications with engineers and account managers at Eclipse in Albuquerque, New Mexico.
Applied DayJet's brand to the fleet of 1,400 aircraft while complying with FAA regulations - every livery decision had to satisfy both visual identity and aviation safety standards.
Storyboarded user interactions, flows, and use cases derived from performance gap analysis across the customer journey.
Provided UX direction across the full surface area - desktop, mobile, kiosk, microsites, CMSs, and emergent AI/ML needs in the operations stack.
Outcome
Six years of single-owner consistency across one of the most ambitious aviation operations of the 2000s. 1,400 aircraft branded. A working reservations system on .NET. Twelve internal applications shipped. Customer journeys storyboarded against analytics-derived gap data, not assumption.
For an investor evaluating Dylan today, this is the case study that demonstrates one specific thing: the willingness and ability to own a creative + front-end surface end-to-end, in a regulated, high-stakes industry, for years at a stretch.
Thinking
The operator's mind, written down.
Short essays on how I run product, build teams, and make build-vs-buy decisions in 2026. Working notes from a 25-year operator.
I've been building products since 1998 and managing them as a discipline since 2014. Across DayJet, BluePoint, PreAsk, LandTech, Avanquest, Walmart Global Tech, and now Tierso - every team I've owned has converged on the same four loops, and on one operating principle that doesn't bend.
The principle
The operator does the job before they lead the job.
I won't put a Product Manager on a workflow they couldn't ship themselves if the engineer disappeared tomorrow. That doesn't mean every PM has to write production code - it means every PM has to be able to own the workflow they're directing. The fastest way to lose credibility with a team of senior engineers is to be a manager who can't read the system. The fastest way to win it is to demonstrate that you can.
Every job I've now led, I've done. UX/UI. UI Developer. Product Strategist. Product Manager. Head of Product. CEO. The five-role lineage is real, and a CEO who has never lived inside any of those layers will quietly lose every conversation that matters.
The four loops
Loop one - the discovery loop. Stakeholder interviews, competitive analysis, system audits, gap analysis. Persona work. Conversion-path teardowns. Most teams skip this when they're under pressure, and that's exactly when skipping is most expensive. At BluePoint, the SkyView product survived contact with $3M-to-$15M annual-account clients precisely because we'd done the discovery work before writing any code.
Loop two - the strategy loop. Product Roadmap, KPIs, OKRs, quarterly initiatives, release planning. The discovery loop's job is to surface the truth; the strategy loop's job is to commit to a sequence of bets given the truth. Discovery without strategy turns into research theater. Strategy without discovery turns into hopeful Gantt charts. Both happen, both fail, both are avoidable.
Loop three - the execution loop. Backlog grooming, sprint planning, user stories, acceptance criteria, bug logging - all in Jira (or whatever system the team has chosen and committed to). The execution loop is where most product work actually lives. It is also where the operator's craft becomes visible: an Epic that's right-sized for the team, an Acceptance Criteria written so unambiguously the engineer doesn't need a meeting to clarify it, a Sprint Goal that survives contact with a stakeholder mid-week.
Loop four - the measurement loop. Power BI dashboards, Google Analytics, A/B test outcomes, conversion-rate evaluations, performance and analytics review. At Avanquest I ran this loop quarterly against Oracle data; at Walmart, the $3M savings figure came out of this loop. The measurement loop is what closes the cycle and re-feeds the discovery loop. Without it, you don't have product management - you have shipping.
What this looks like in practice
I structure my weeks so each loop gets attention without crowding out the others. I expect every PM I lead to do the same. The team's quarterly OKRs map cleanly onto the strategy loop. The sprint cadence maps onto execution. Discovery happens deliberately every quarter, not opportunistically. Measurement is a standing weekly conversation, not a quarterly retrospective.
This approach has produced quotable outcomes - $3M saved at Walmart in 6 months, three AI/ML products owned at BluePoint, a 1,400-aircraft brand identity at DayJet, a Network Orchestration platform launched as a founder. What it produces more reliably than any individual headline is something subtler: teams that ship the right thing on a predictable cadence, in a regulated environment or a frontier one.
Most product leaders specialize early. They pick a role - UX, engineering, strategy, management - and climb. By the time they're CEOs they've forgotten what the work feels like at three of the four layers underneath them.
I went the long way. The five-role lineage is what I call the path I actually walked, and what I now use as the lens through which I evaluate every product person I hire or invest in.
The five roles
UX / UI. The discipline of figuring out what the workflow is supposed to feel like - for the actual person doing it, on the actual surfaces they use, in the actual conditions of their day. I learned this in 1998 at Foster Tech and refined it across DayJet (1,400 aircraft + 12 internal apps), Kitara, BluePoint, and LandTech. UX/UI work that ignores the operator's reality is decoration.
UI Developer. Being able to ship the front-end yourself. HTML5, CSS, JavaScript. The .NET reservations system at DayJet. The HTML5/CSS-on-Java-framework work at Kitara. The browser-side discipline matters not because every executive should be writing production code, but because you cannot lead what you cannot read. A Head of Product who can't read a pull request is a Head of Product who is being managed by their senior engineers, not the other way around.
Product Strategist. The market-facing layer. Competitive analysis, gap analysis, persona definition, opportunity sizing, go-to-market planning, business-objective translation. 15 years and counting. This is the layer where the discovery loop lives. Without strategy, the product team has velocity but no direction.
Product Manager. The execution layer. Roadmaps, OKRs, KPIs, release plans, sprint planning, backlog grooming, acceptance criteria, bug logging. 12 years on this layer. This is also the layer that has the highest bullshit-tolerance threshold in the industry - every PM job description claims this layer; not every Product Manager actually does it. The work of a real PM is unglamorous and constant.
Head of Product. The systems layer. Multiple PMs reporting in. Strategy across a portfolio rather than a product. Cross-functional alignment with Engineering, Design, Sales, and Customer Support. Mentoring and leveling. Hiring. At Walmart Global Tech I led 12 Product Owners across the US and India under this lens; the $3M cost savings outcome lived at this layer, not at any individual PM's desk.
Why the lineage matters
Three reasons.
One: it makes hiring honest. When a candidate tells me they're a Product Strategist, I can tell within ten minutes of conversation whether they actually are one or whether they're a Product Manager who likes the title better. Living each layer means I can tell them apart cold.
Two: it shapes how I assemble teams. A great team needs all five layers represented, but not every layer needs a permanent FTE. UX/UI and UI Developer can rotate or sit with one person. Product Strategist and Product Manager are two different jobs - most teams that flatten them into one job underperform. Head of Product is necessary above three PMs and unnecessary below.
Three: it gives investors a clear way to read me. When a partner or investor evaluates Tierso, they're really evaluating my judgment across all five layers, not just my title. The lineage is how I prove I have it.
What I look for
The people I want to work with - at Tierso, on advisory boards, in partnerships - share two characteristics. They've done at least two layers in the lineage themselves, and they can identify which layer they're operating in at any given moment without being asked.
The first half of that filter is about earned credibility. The second is about meta-awareness. Both are non-optional.
If you've read this far and recognized yourself, the is right there.
Award-winning product leader with 24+ years in software development and product strategy, contributing $15M+ in revenue growth through scalable, user-centered digital products. CEO of Tierso. 60+ products shipped across SaaS, PaaS, and cloud-based platforms.
Career stats
27
years UX / UI
26
years front-end dev
25
years software dev
17
years R&D
15
years product strategy
12
years product management
Roles held
CEO · Head of Product · Sr. Product Manager · Sr. Product Owner · Business Owner · Strategist · Sr. UX Designer · UX Information Architect · Web Engineer · Front End Developer · Creative Director · Research Strategist
Industry experience
Aviation · aircraft design · IT solutions · automotive tech · ad-tech & monetization · title and asset transfer systems · enterprise search · cybersecurity · network orchestration · banking · exchange platform systems · blockchain · data management. Adaptable for crypto compliance, DeFi governance, and tokenized ecosystem challenges.
Experience
Founder & CEO · Tierso
2024 - present
AI development · Network orchestration · Full-stack engineering
Founded an embedded engineering firm operating at enterprise scale: 2.4M AI requests/day at 99.2% accuracy, $4.2B daily exchange volume, 18 modules behind one API gateway, 200+ years combined team experience.
Defined the three-pillar service architecture (AI / orchestration / full-stack) and the unified API gateway model that ties them together.
Tagline: Build Faster. Scale Smarter. Win Bigger.
Technical Product Manager · LP Media & Design - West Palm, FL
Mar 2024 - present
Content Management System · Mobile products
Responsible for client relations, scope of work, development roadmap and project budget for Mobile Products.
Conducted System Audits and Competitive Review for product Competitive Strategy.
Produced Scope and Product Roadmap presentations to review proposed solutions with staff and clients.
Gathered project requirements to write Epics, Stories, and development tracking utilizing Jira.
Owned all branding efforts and User Experience projects for DayJet's Agile development teams.
Graphically designed and maintained DayJet's e-commerce reservations system and 12 internal applications on .NET.
Collaborated on aircraft configuration with engineers from Eclipse, BMW, and Pontiac for 1,400 Eclipse 500 aircraft - the largest non-military aviation order in world history at the time.
Applied DayJet's brand to the fleet of 1,400 aircraft in compliance with FAA regulations.
Continuing education: Blockchain / Ethereum Training · ITIL · MS TFS · Scrum · Agile · RT3D.
Trust
Verifiable. By design.
What's documented
Award-winning product leader, 24+ years software development.
$15M+ in lifetime revenue contribution across 60+ digital products.
$3M saved in the first 6 months launching the Walmart Data Portal.
1,400 Eclipse 500 aircraft branded for DayJet - largest non-military aviation order in world history at the time.
Founder of Tierso (tierso.com) and PreAsk (preask.com).
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