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👋 Hello

I’m a people-first, remote-first product leader with 20+ years of experience leading empowered teams across a variety of B2C, B2B, and Developer Platform industries. Here’s a TL;DR summary of my career:

  • I have extensive experience growing products and leading teams in all stages of the business, from pre-product/market fit through product-led hyper-growth to integrating with sales-led enterprises.
  • Over 7½ years at Postmark (email delivery infrastructure for developers) I helped grow the product from $1.7M in ARR when I joined in April 2016 to over 23,000 paying customers and over $12M in ARR by the middle of 2023. Postmark is a much-loved product with an NPS score of 80.
  • I believe in fostering cultures and software development processes that help teams do the best work of their lives in environments that are safe, healthy, and fulfilling.

There’s a bunch more detail below, but you can also view a summary on LinkedIn and take a look at my Manager README on Github. If you like side projects, check out the site where I track my music listening.

How I work

Before we get to the work history I wanted to share at a high level what areas I specialize and thrive in. The goal is to showcase how I work with teams to drive customer and business growth depending on the specific needs of a product and team. Here’s where I mostly focus:

  • Product and growth leadership: Building and coaching empowered teams in safe, fulfilling environments. Developing systems and structures for teams to have the strategic context they need to move quickly to meet the needs of customers and the business. Ethical focus on growing revenue sustainably.
  • Product management: Developing product vision and strategy, making sure teams work on the right opportunities for customers and the business, designing systems to facilitate quality execution and delivery. See my book Making It Right: Product Management For A Startup World for more on my product philosophy.
  • Team topologies and development process design: Understanding the needs of developers and the rest of the business, and collaborating with engineering leaders to design a team structure and development process that fits the culture of the organization and gets everyone involved in an appropriate way.
  • User experience research & design: I’ve done everything—and work to keep these skills up to date—including ethnography, heuristic evaluations, usability testing, participatory design, concept testing, and surveys. Content audits, style guides, and content creation. Flow diagrams, wireframes, interactive prototypes, and concept development.

If you’d like to find out more or discuss working together, you can view my LinkedIn profile, or send me an email. All right, onto the specifics.

Cloudflare (April 2024 – Current)

Director of Product

I support the Data team at Cloudflare. Our team exists to make the data that is generated by our products simple to use and always secure, available, and insightful for customers and Cloudflare teams.

I am responsible for:

  • Growing and coaching a team of Product Managers to support our data efforts.
  • Long-term product strategy and shorter term roadmap development and execution, alongside our Engineering Managers.
  • Showing and growing the business value of our data platform, both with internal teams as well as customers.

PagerDuty (November 2023 – March 2024, continued from acquisition)

PagerDuty acquired Jeli.io in November 2023. The Jeli team joined PagerDuty.

Director of Product

I led one of the product teams responsible for the integration of Jeli with PagerDuty.

Worked across business units to develop a strategy and roadmap for integrating Jeli’s post-incident review tools into the PagerDuty Operations Cloud to drive increased revenue. Accountable for revenue targets through a combination of product development and Sales enablement. We released the first iteration of the PagerDuty + Jeli integration in Q1 2024 (see Build More Resilient Operations with PagerDuty Incident Management), after which I decided to take on a new opportunity.

Jeli.io (August 2023 – November 2023, continued at PagerDuty after acquisition)

Head of Product

Accountable for the strategy and growth of Jeli’s 3 product pillars: Incident Response, Incident Analysis, and Cross-incident Insights. During this time I worked with the team on the following areas:

  • Created a product strategy that includes a definition of our vision and goals, strategic differentiation, growth strategy, GTM strategy, and how the product will assist with growth.
  • Created a team topology for the way our teams will deliver value going forward, along with several structured ways for us to plan and prioritize the work we do (see Why using a Now/Next/Later roadmap might be right for you).
  • Launched several near-term initiatives to assist with growth, including onboarding improvements, content marketing initiatives, and product improvements.

I continued this work at PagerDuty, following its acquisition of Jeli.

Postmark (April 2016 – August 2023)

I started with Postmark as the team’s first product manager, and ended my time with the team in a General Manager role following its acquisition by ActiveCampaign. Over 7½ years I helped grow Postmark from $1.7M in ARR when I joined in April 2016 to over 23,000 paying customers and over $12M in ARR by the middle of 2023. Postmark is a much-loved product with an NPS score of 78.

Here are some blog posts I’ve written about my work on Postmark:

Here are some blog posts I wrote for some of our bigger releases:

With that overview out of the way, I’ll now go into the fairly confusing reverse-chronological timeline of how this all worked. The big thing to keep in mind is that Postmark is one of the products we built at Wildbit. Buckle up…

Organizing the wall

ActiveCampaign (April 2022 – August 2023, continued from acquisition)

ActiveCampaign acquired the Wildbit products Postmark and DMARC Digests in April 2022. The majority of the Wildbit team joined ActiveCampaign.

General Manager (GM) of Postmark (October 2022 – August 2023)

GM and part of the Senior Leadership Team at ActiveCampaign. Accountable for the day-to-day operations, outcomes, and growth for all of Postmark.

I led Product, Design, Marketing, Sales, Customer Success, and Ops (~20 people), and we collaborated closely with the Engineering team to address customer opportunities in a way that builds a healthy business within the ActiveCampaign ecosystem.

Head of Product, Postmark and DMARC Digests (April 2022 – September 2022)

I led the cross-functional team responsible for the transition and the successful integration of Postmark within ActiveCampaign (transactional email automations, event triggers, and more).

Wildbit (April 2016 – April 2022, continued at ActiveCampaign after acquisition)

Head of Product (Jan 2020 – April 2022)

I was responsible for team development, product vision, execution, growth, and product culture across all Wildbit products (Postmark, DMARC Digests, People-First Jobs, Beanstalk). This included:

  • Accountable for revenue and product growth as part of the Executive Leadership Team.
  • Defined and drove the execution of the product strategy for all Wildbit products, ensuring a sustainable product-led business.
  • Developed and coached an empowered product and design team, with a strong focus on living out our principles and values in the work we do.
  • Expert on modern forms of product planning, customer research and discovery, product discovery, and product development processes, to coach and guide the team effectively.
  • Responsible for pre-sales and continued product marketing with potential and existing customers.
  • Responsible for privacy and compliance.

Principal Product Manager (Apr 2016 – Dec 2019)

I was hired as Wildbit’s first Product Manager to define and implement the Product function within the organization. I facilitated the creation of the first Product Strategy for Postmark, as well as the processes and rituals we used as an empowered team.

I led the project to successfully transition the Postmark business from a credits-based pricing model to more profitable and sustainable monthly plans and tiers. I also led the project to introduce bulk email sending to Postmark in addition to our existing transactional email capabilities, which vastly expanded our total addressable market.

In short, I oversaw our product lifecycle from start to finish. I was responsible for making sure we work on the right customer and business opportunities, come up with the right solutions to address those opportunities, ship those solutions and improvements regularly to customers, and ensure that customers discover and adopt the product and its various features.

Postmark customer journey

Jive Software (October 2014 – April 2016)

Director of Product Design

I was a product design lead on Jive’s suite of mobile apps. I specifically worked on the following areas:

  • Fulfilled a variety of roles on Jive’s mobile products, including Lead product designer on Jive Daily (Jive’s primary mobile app), Lead product designer on Jive Circle (a corporate directory app), Product designer on Jive Chime (a real-time team messaging app).
  • Activities included user research, product discovery, information architecture, content strategy, interaction design, and prototyping.
  • I was also responsible for all user research at Jive, including ethnography and usability testing on our mobile and desktop software. Here’s a post I wrote about how we do mobile testing: The logistics of usability testing on mobile devices.

Below is the final version of the Information Architecture document I created for the Jive Circle app. We made sure that we all agreed on the overall IA (and what’s going to be in the Alpha version) before I started with Interaction Design.

I then proceeded to create a prototype in Proto.io. You can view and play around with the version of the prototype we used for visual design and initial develpoment by clicking on the link below (open it in a new window):

Jive Circle Prototype v5

Here’s a snapshot from November 2015:

Below is an example of user journeys I worked on. In this case I helped the team to create personas for a Support solution, and we used that to define the journeys for each persona before going into the design phase.

HealthSparq (April 2014 – September 2014)

Director of Product

I led and grew the Product & Design team for all Healthsparq products. Responsible for hiring, product strategy, design process, and day-to-day execution and delivery.

I led the product and design teams through the release of the first version of our Unified Search product in August 2014: a single interface to search for health care providers and costs, bringing an e-commerce experience to health care. I was responsible for product strategy, prioritization, roadmap planning and execution, process improvements, and feature definition/design/development throughout this project.

I worked with the team to create a design process that will work for us and the unique needs of the organization. Here’s what we settled on:

Design Process

On the Product side I worked to define and deliver the first version of our Unified product to bring e-commerce style shopping to health care. Here’s a small part of our first whiteboarding session to define the healthcare customer journey:

Journey

And here’s a view of the story map we created to define our first release of the product:

Story map

We also created a bunch of personas to help us stay focused on user needs. Here’s a small section of one of them:

Personas

And here’s a section of the home page for the first release of the product (graphic design by HealthSparq design team member):

Home

Flow Interactive (May 2012 — March 2014)

Director of User Experience

I was responsible for user experience design & strategy projects, business development, and training. This included:

  • Finding and securing new clients for the business, and maintaining positive client relationships.
  • Client and project management on several UX projects simultaneously, including management of the internal team on each project.
  • A variety of hands-on user experience design activities, including usability testing and user research, information architecture, content strategy, and interaction design.
  • Development and conducting of training on User Experience Design and Product Management

Here are some selected projects I worked on:

  • Direct Axis — contextual interviews, personas, customer journey mapping, UX strategy
  • Juniva — personas, customer journey mapping, interaction design, graphic design, front-end development (see juniva.com)
  • Obox — usability testing (see the client’s write-up of the process)
  • Vumi Go — personas, customer journey mapping, interaction design, usability testing, graphic design (see Case study: redesigning Vumi Go)
  • Virgin Active — usability testing
  • ificould — information architecture, interaction design (see ificould.co.za)
  • Primedia — user research, UX strategy, concept development
  • Discover Africa — Product Discovery and UX strategy
  • Design Indaba — Product Discovery and Product Management coaching
  • Takealot — personas, customer journey mapping, interaction design, graphic design (in development, not live yet)
  • Mr Delivery — personas, customer journey mapping, IA and content strategy, interaction design, graphic design, front-end development (in development, not live yet)

Below are some images that show our work process on selected projects

Initial interface sketch:

Vumi initial

Prototype in Axure:

Vumi prototype

Persona workshop aftermath:

Persona board

Sketch for a new checkout process:

New checkout sketch

Note-taking during research:

New checkout sketch

Analysis after research:

Analysis

Initial customer journey sketch:

Journey sketch

Final customer journey, on client’s office wall:

Customer journey final

kalahari.com (December 2010 – May 2012)

Head of Product Management and User Experience Design

Check out Case study: the user experience of kalahari.com, one year later, in which I go over many of our accomplishments in 2011.

Led the 13-person Product & Design team responsible for the end-to-end user experience of kalahari.com. This included Product Management of all front-end and backoffice product lines in the kalahari.com ecosystem through their entire lifecycle (vision, strategy, design, delivery, measurement, and maintenance).

Here are some selected projects I led my team through:

  • Established a successful product development process from idea conception and prioritization to processes for design cycles, functional specifications, and technical implementation
  • Introduced a systematic approach to user-centered design, including user research and UX-driven interaction & visual design
  • Created the Product Council, a cross-functional body of leaders who steer the prioritization and roadmap for kalahari.com
  • Ongoing redesign of the entire kalahari.com front-end through regular, incremental improvements to the user experience.
  • Facilitated user experience and product management workshops with sister companies in Cape Town and South-East Asia.
  • Some success metrics:
    • Checkout redesign: 7% increase in completion rate
    • Registration redesign: 18% increase in completion rate

Selected artifacts from projects

Customer journey map:

Kalahari journey

Development process:

Kalahari PDLC

Wireframe for Checkout redesign:

Checkout wireframe

Final Checkout redesign (produced by Visual Designers)

Checkout Visual Design

Yola.com (October 2009 — November 2010)

Product Manager and user experience designer

Led the team responsible for the product vision, strategy, design, and development of a variety of areas of the Yola user experience. Here are some projects I worked on:

  • Main website: Led the redesign of the Yola website, resulting in a 25% increase in first-time visitor sign-up conversion and a 10% decrease in bounce rate
  • User account area (My Yola): Led the redesign of My Yola from basic sites listing to full-fledged account and site management area
  • All payment/checkout flows: Led the redesign of payment screens that resulted in 28% increase in completion rate for domain purchases
  • Sign up and user onramp: Led redesign of sign-up flow that resulted in 44% increase in the number of websites published with Yola
  • Revenue-generating products (e.g, bundled packages): Led design and implementation of a revamped Pro package that resulted in a 280% increase in revenue from the package

Below are some artifacts from the different projects.

Flow diagram for redesigned bundled packages purchase flow

Yola flow chart

High-fidelity mockup for new home page (produced by Visual Designers)

Yola home page

eBay (April 2005 – October 2009)

Senior Manager, Product Health and Strategy

  • Responsible for the planning, execution, and business impact of eBay’s Product Health program, which is a holistic research program that drives global product strategy and resource allocation through insights from a variety of user assessments of our site experience. We used surveys, true-intent studies, advanced in-page analytics, site logs/ web analytics, and qualitative insights.
  • Managed the team that executed the program, and worked with leaders across the design, business, and engineering organizations to develop product strategy based on the insights, as well as provide success metrics to measure the impact of product changes.
  • Collaborated across functions to write and scope specifications for new products and changes to existing features, from product discovery through execution & delivery.

Manager, User Experience Research

  • Developed, and built the team responsible for, eBay’s Product Health program.
  • Managed the team responsible for all qualitative and quantitative user experience research related to the Selling business.

Staff User Experience Researcher

  • Responsible for all product survey research in the User Experience Research group at eBay
  • Designed and started executing eBay’s Product Health program, a comprehensive program to prioritize and guide product strategy and enhancements.

Senior User Experience Researcher

  • Responsible for all product survey research in the User Experience Research group at eBay.
  • Even mix between executing the research myself and managing vendors and internal resources to complete projects.
  • Work directly with designers, product managers, marketers and engineers to develop and execute high-quality research using the most appropriate methodologies.
  • Includes design, fielding, extensive analysis and reporting on results. Combine survey research with usability tests, ethnography and other qualitative methods.