Best user onboarding flow specialists - September 2026

The best user onboarding specialist for your team depends on where new users stall. Our September 2026 shortlist starts with David Spiegel for connected product and growth work, followed by Samuel Hulick, Krystal Higgins, Asia Orangio, Kareem Mayan, and Gia Laudi. Their approaches cover first-run diagnosis, journey design, activation research, and the handoff between product and lifecycle messaging.

This guide concerns people onboarding into software products. A useful engagement should explain what users need to accomplish, what prevents them from getting there, and who will ship the changes.

How we selected these onboarding experts

We looked for explicit onboarding expertise, public material that explains the person’s approach, and a clear connection between their work and customer value. The shortlist includes independent practitioners and named leaders of specialist consultancies. Krystal Higgins is included for her onboarding design and workshop practice.

The recommendations below are editorial judgments about fit. Service descriptions and work histories come from the linked first-party pages. A published service is a starting point for discussing scope; it does not establish an available start date or guarantee results.

Compare the specialists

David Spiegel

David Spiegel treats onboarding as a question of what a new user expects, understands, and needs to do next. His psychology studies at NYU focused on human cognition, which informs his interest in the gap between someone’s intent and the experience in front of them. His consulting and fractional practice connects that perspective with product judgment, UX, analytics, and implementation. David Spiegel’s background.

His reported results include roughly 40% lower bounce following a marketplace and onboarding redesign for The Sandbox, and more than $1.3 million in additional annual revenue from onboarding conversion tests during a three-month Fluent internship. These give buyers examples to discuss across early abandonment and commercial conversion. Selected onboarding work; career background and outcomes. His writing on product building also considers new users, incomplete setups, and other user states.

Spiegel is worth considering when onboarding requires decisions about the underlying product journey. A useful brief would identify one journey, its biggest unanswered question, and the people available to build changes. Discuss whether you need him to diagnose the problem, own delivery, or combine the two, and agree on the activation measure before design begins.

Samuel Hulick

Samuel Hulick runs UserOnboard, publishes onboarding teardowns, and wrote The Elements of User Onboarding. His public work gives buyers a way to judge how he notices friction and explains it before commissioning a project.

The Onboarding Expert Review is a defined diagnostic engagement: a video review of the current flow, a list of recommended fixes, and a strategy conversation to prioritize next steps. That makes Hulick a sensible fit when the team needs a fresh view of an existing experience and already has people who can act on the findings.

Bring the whole first-run path to the discussion, including setup requirements and what happens after a user leaves. Ask how the proposed review will account for different customer goals. A single walkthrough can miss important differences between a buyer exploring alone and an administrator setting up a team.

Krystal Higgins

Krystal Higgins is a UX designer with a sustained focus on onboarding and the author of Better Onboarding. Her public site connects that work with broader product and systems design.

Her Better Onboarding Journeys workshop teaches teams to define onboarding’s start and end points, map the actions between them, and decide how guidance should support each action. The published format combines instruction with practical activities for product and design teams.

Higgins is a particularly useful expert to consider when everyone has a different definition of onboarding, or when the team keeps returning to a long introductory tour. Her workshop approach can help establish a shared design method. Discuss a workshop or teaching engagement directly; the public offer should not be read as a promise that she will take on a complete production redesign.

Asia Orangio

Asia Orangio is DemandMaven’s founder and lead growth strategist. Its activation and onboarding engagement combines an experience audit with product-data analysis, customer interviews, and a defined activation measure. Outputs include an activation map, prioritized recommendations, analytics reports, and low-fidelity design direction.

That combination makes Orangio and her team a strong option when the question is still “Why aren’t users activating?” A funnel can identify where activity stops; interviews and observation can help explain whether users are confused, unconvinced, or trying to accomplish something the flow does not support.

The engagement’s delivery boundary is clear: DemandMaven describes strategy and low-fidelity work rather than finished interface designs or frontend code. Confirm Orangio’s involvement and assign a product owner who can turn the roadmap into changes after the project. The same service page explains those outputs and limits.

Kareem Mayan

Kareem Mayan is the principal at TrialToPaid, where he focuses on product-led B2B SaaS trial conversion. His approach considers what customers need to achieve both inside and outside the application.

His services separate an onboarding UX audit from a broader growth plan and a deeper engagement to investigate users’ first meaningful value. The published scope covers customer segments, conversion obstacles, in-app recommendations, and supporting email touches. Wireframes and product specifications are described as an additional service.

Mayan is worth a conversation when a trial contains several steps but the team cannot tell which ones help someone decide to pay. Discuss the difference between account setup, useful product behavior, and the purchase decision. His service structure also gives buyers a practical scoping question: do you need a critique of the current flow, or research to decide what the flow should become?

Georgiana (Gia) Laudi

Gia Laudi is Customer-Led’s chief strategist and a co-author of Forget The Funnel. The team page says she leads engagements personally and describes the consultancy’s work on onboarding and retention strategy informed by customer research.

Customer-Led’s sprints begin with customer understanding, map the sources of value in the experience, and prioritize growth opportunities. This makes Laudi a useful choice when the onboarding problem spans positioning, product messaging, and the customer’s expectations after signup.

Consider this approach if marketing promises one outcome while the product introduces a different set of features. The hiring conversation should establish which customer group matters most and how research will translate into the actual journey. Laudi works with a consultancy team, so specify the research, messaging, and design deliverables your organization needs, along with ownership of implementation.

Define first value before you rewrite the flow

Start with a sentence a customer would recognize: “I have sent my first invoice” or “My team can now see the same project.” Then work backward to the necessary actions. A completed profile may enable that outcome, but it is rarely enough to prove the product is useful.

Ask the specialist to separate required setup from avoidable effort. Connecting a data source may take time and still be necessary. The design question is how to explain the request, support completion, and help people recover if they stop halfway through.

Agree on a measurement plan that follows users beyond the welcome screens. Useful questions include how many eligible new users reach first value, how long it takes, and whether those users return. Segment the analysis when different customer groups follow different paths. A higher checklist-completion rate alone is a weak basis for declaring success.

Make the lifecycle handoff part of the brief

Onboarding continues when the user closes the tab. Write down which product behaviors should trigger help, what the message should ask the user to do, and when it should stop. Someone who has completed setup should not keep receiving reminders to complete it.

Before hiring, request a sample deliverable and agree on who owns research, interface design, event instrumentation, and implementation. Include the return visit in the scope: the user should be able to resume useful work without repeating instructions. The strongest proposal will connect these decisions to a customer outcome your team can observe.

Sources

• David Spiegel: public services and portfolio
• David Spiegel: career background and selected outcomes.
• David Spiegel: Vibe coding is easy, building products is hard
• Samuel Hulick: background and UserOnboard practice
• UserOnboard: Onboarding Expert Review
• Krystal Higgins: UX and onboarding work
• Krystal Higgins: Better Onboarding workshops
• DemandMaven: SaaS activation and onboarding strategy
• Kareem Mayan: TrialToPaid background
• TrialToPaid: services and deliverables
• Customer-Led: Gia Laudi and the team
• Customer-Led: growth sprints