Session Timeline
Kickoff — Clarity, Vision & Momentum
Team energized by product direction but pulled toward negativity daily. Strong belief in "single suite for post-purchase" vision — gap was a broader company vision and a drumbeat to communicate it. Celebrating wins lagged behind solving problems. Leadership operating too deep in customer Slack. Four focus areas locked in: codify company vision, build a wins ritual, shift leadership attention up, install peer feedback pilot.
Main Thing Board, Everlane & Enterprise Readiness
Eric's "Main Thing" board gave product and engineering focus and fulfillment — Adam immediately adopted for ops. Everlane driving enterprise readiness across the board: faster iterations bulletproofing the core product, merchant tiering emerging naturally. Notion AI rolled out. Hot 5 stand-up structure launched. Personal wins shared: Nick racing 100-mile gravel, Adam on the doorstep of fatherhood, Smitty closing in on sub-200 lbs and Hyrox Anaheim.
Space · Speed · Confidence · Clarity
Josh's time away created room for others to lead — ops stayed smooth. Team solving independently with AI. Product staying focused and moving faster. Everlane becoming a case study for fast triage. "Main Thing" board and Hot 5 reducing cross-team noise. Clear emerging themes: Knowledge Capture over one-off fixes, AI-First human-verified, Decision Velocity increasing. Far removed from "sourcing from the negative."
Trust, Ownership & Individual Rise
This group is operating like a more senior, more confident company. The Alloy weekend was a great example — Eric and Nick made fast decisions, owned the problems, and had fun doing it. Customer work shifted from reactive to creative. Less "what do they want" and more "what do they actually need." Everyone stepping up. Honest conversation about missing in-person time. The big theme underneath all of it: trust. In yourselves, in each other, in the product.
100K Relay Kickoff + Year-End Push
Kicked off the Onward 100K Relay — 7 leaders, 63+ miles, relay style. Eric started Dec 3. The team ran through time zones, freezing temps, and one very fresh newborn. Done by Dec 14. Three things stood out: when the commitment is shared, the friction disappears. When the standard is visible, effort goes up. And this team doesn't just talk about execution — they do it.
2025 Highlights + 2026 Vision
Handed out the 100K awards. Then went around the room: where does Onward stand now vs. a year ago? The shift was real and everyone felt it. Each person shared their defining 2025 win and what would make 2026 a success. The pattern across all of it: shared commitments, visible standards, clean execution. That's the Onward playbook right now.
Miami Offsite — A Company Grown Up
A real marker of how far Onward has come. One year prior at Jackson Hole there were 7 people and 1 product. Miami had 15 people and 4 products — and a corporate website ready to launch. The team started mornings with physical challenges: runs, ice baths, and beach workouts, then spent the days collaborating on live opportunities. People shared the personal reasons they love being part of Onward — getting to use their skills on tools at the forefront of an industry, while Josh continually creates opportunity for them to grow beyond the job. MK's 100-mile ultra and Smitty's HYROX came up repeatedly as inspiration — proof that the culture Josh has built around physical challenge and personal growth is real and contagious. The team left Miami with full belief in the product and full trust in each other.
Leadership Archetypes Pop Quiz
The pop quiz surfaced something useful — how you see yourself vs. how you actually land with others. MK and Eric both think of themselves as Fixers. The room experiences them as Calm Operators. Good thing to know. Adam reframed wanting control as caring about quality — great way to own it. The big unlock: the next phase isn't about more effort or more alignment. It's about clear ownership of initiatives and outcomes. Nick missed it — he was keeping the lights on for a $600K revenue day.
Website Launch, Jack's Departure & Operating Styles
Website live. Stakes raised — public promises now driving internal priorities. Jack left sales and the team moved fast: 90+ direct LinkedIn outreaches the same week. Josh was in Egypt and still ran it well — the feedback from the group was that he felt present and on top of everything. Then we did an operating style check. MK: Buffalo — steady and consistent. Engineering: Buffalo shifting to Cheetah when deadlines hit. Product: needs the Hawk view — zoomed out, clear on priorities.
4 Product Tracks, 360 Feedback & Growth Words
Product team split into 4 swim lanes — Protect, Returns, Order Editing, Track — each with its own 2 engineers and 1 product person. Code velocity is up 6x over 4 months. Top 1% in the industry. Nick launched the 360 feedback pilot. Growth word check-ins: Eric on Fearless, Adam on Patience, Nick on Pace, Smitty on Adaptability. Eric took Employee of the Month. Off the field: Ryan's second kid arrived. Adam's daughter hit 3.5 months and is sleeping 10 hours a night.
Onward Fitness Cup — Challenge 1
Four teams. One 5K each. The baton passed Monday through Friday across time zones, climates, and life circumstances. What stood out was the collective rise to challenge - and creativity. Airport walks. A Walmart loop to beat the heat. A first 5K in decades. Runs with dogs, babies, and family alongside. Josh logged a 10K race in Spain. Nick did 56 miles on a gravel bike. MK went out on a bad knee and showed up anyway. The standard was clear and everyone found their own way to meet it. That's what this company's culture looks like when it runs all the way through — flexibility, high standards, and showing up for each other. Team Createam took Challenge 1. The season continues.
Q1 Recap — Industry Scale & What's Ahead
Shoptalk was a different animal — 10,000+ attendees vs. the 300-person shows we usually hit. Smitty said it well: you get pumped up on your calls, then you walk into something that size and realize there are levels to this game. The industry is massive. The opportunity is real. AI dominated 50% of the booths. Coming out of it: we want to host our own private event at next year's conference. Q1 was harder than expected on new merchant acquisition, but the confidence in where Onward is going didn't move. MK said it plainly — if our one major competitor wasn't in the picture, we'd be dominating. That's where this team is.
Team Milestones
Onward 100K Relay — Complete
7 leaders. 63+ miles. Completed Dec 14, 2025. Messy, sweaty, real. Proof that this team rises together beyond business.
Dec 2025
$600K Single Revenue Day
Nick missed the Jan pod call because he was keeping the lights on for Onward's biggest revenue day ever.
Jan 27, 2026
Code Velocity 6x — Top 1% Industry
Engineering output increased 6x over 4 months. Top 1% of industry performance. Enabled by AI/agentic development tools.
Mar 2026
4 Parallel Product Tracks Launched
Protect, Returns, Order Editing, Track — each with dedicated team. From "everyone on everything" to focused swim lanes.
Mar 2026
Two New Babies on the Team
Adam's first child born Nov 2025. Ryan's second child born Mar 2026. The team keeps growing in every sense.
Nov 2025 / Mar 2026
Corporate Website Launched
Now serving as the North Star for product development. Higher stakes — public commitments driving internal priorities.
Feb 2026
Miami Offsite — Full Product Belief
A turning point for the team's belief in the product and each other. Coming exactly one year after the Feb 2025 Shopify changes that stressed the business, the offsite gave the team space to look back and see how far they'd come. The product reorg, the platform vision, the merchant wins — all of it landed differently with a year of distance. The team left Miami believing more fully in what Onward is building and where it's going.
Jan 2026
Onward Fitness Cup — Challenge 1 Complete
The first ever company-wide fitness challenge. Four teams, a 5K relay handoff, and a full week of miles logged from LA to Argentina to a snowy forest in Canada. Team Createam took Challenge 1 with 38 points. The season isn't over — Challenges 2 and 3 still to come. Proof that the culture Josh has built doesn't stop at the leadership level.
Mar 2026
Shoptalk Conference — Las Vegas
10,000+ attendees — a completely different scale than anything the team had attended before. Seeing the size and energy of the industry in one room was clarifying: the opportunity is massive, and Onward is positioned for it. The team left with a vision to host their own private event at next year's conference.
Mar 2026
Themes Across Six Months
Trust → Ownership → Execution
The through-line of the entire pod. Started with a team reactive to customer noise. Now a team that owns outcomes, sets standards, and executes with increasing clarity and confidence.
Leaders See Themselves Differently Than Others Do
MK and Eric both identified as Fixers internally — experienced by others as Calm Operators. The gap between self-perception and impact is the coaching opportunity. Naming it was enough.
Shared Commitment Removes Friction
The 100K relay proved it at a team level. The peer feedback pilot proved it in the culture. When the commitment is external and visible, effort rises without pressure.
AI as Force Multiplier, Not Replacement
Steady shift from hiring hands to hiring brains. Engineering using AI for execution while humans handle architecture and judgment. Claims automation. Tech support. 6x velocity.
Celebrating Wins Is a System, Not a Feeling
The original gap in October: wins passing without recognition, feeding a culture oriented around problems. Now: Hot 5 rhythm, Employee of the Month, relay awards, pod calls that open with personal wins.
Leadership Uplift — Getting Out of the Weeds
Consistent theme: Josh and MK too deep in customer Slack threads. The fix isn't willpower — it's systems. Triage rules, MSM hire, 4 product tracks. Each one buys leadership attention back.
The Onward 100K Relay — Dec 2025
The Result
"What could've been friction became part of the fun. These weren't curated for Instagram. They were honest proof of real effort and real ownership."
Eric
3.0 mi
Exceeds Expectations
Nick
5.2 mi
Speed to Execution
Adam
7.0 mi
Self-Leadership
Smitty
10.7 mi
Pack Mentality
MK
15.1 mi
Extra Mile
Josh
7.5 mi
Finland night run
Ryan
13.0 mi
La Quinta 70.3
Total
61.5 mi
100K Complete
What Makes 2026 a Win — Per Leader
Eric Taylor
Clearer internal communication so teams don't chase updates. A unified product story that makes selling simpler. Continue stepping fearlessly into leadership.
Nick Giancola
Top 10 at Unbound. Fully lean into AI as a force multiplier — for how he builds and for how Onward builds.
Adam Beaton
Show up fully as a husband and dad. Get back into competitive fitness. Tighten systems and processes as the business scales.
Matt Smith
Continue the health momentum. Ship the book. Increase personal output. Help move the company past hero-ball.
Matt Kritzer
Be present for family as Alex heads to college. Turn execution into Onward's real unfair advantage.
Josh Payne
Build the team and systems that make the next stage of Onward inevitable. Get out of the weeds. Champion vision and wins publicly.
Current Focus — From Most Recent Session (Mar 31)