Rick Knudtson (Workshop): The email signal he ignored for 9 months

Summary of Rick Knudtson (Workshop): The email signal he ignored for 9 months

by Omer Khan

51m•September 3, 2026
Listen to Episode

Overview of Rick Knudtson (Workshop): The email signal he ignored for 9 months

Rick Knudtson, co-founder and CEO of Workshop, shares the gritty origin story behind a company now doing 10M+ ARR with ~140 employees and nearly 1,000 customers. The big lesson: Workshop did not find product-market fit by sticking to the original plan. Instead, after nearly a year of weak traction, the team finally listened to repeated customer feedback about enterprise email communication—and rebuilt the product around that pain point. The result was dramatic: about 3 customers in 9 months with the original product, then 10 customers in 30 days after the pivot.

What Workshop Does

Workshop is an internal communications platform for large companies.

Core use case

  • Helps organizations communicate with employees across:
    • Email
    • SMS/text
    • Slack
    • Microsoft Teams
    • SharePoint / intranets
  • Focuses on:
    • Distribution of messages across channels
    • Analytics and visibility into reach and engagement
    • Governance/security needed for enterprise-scale communications

Why it matters

Large companies often have:

  • Global workforces
  • Many departments and teams
  • Different geographies and time zones
  • Strong IT/security requirements

Workshop is designed to make internal comms more collaborative, measurable, and scalable.

How the Idea Started

Rick’s previous company, Flywheel (a WordPress hosting company), gave him the early insight that internal communication becomes incredibly important as organizations scale.

Key observations from Flywheel and WP Engine

  • Fast-growing companies are constantly changing
  • Remote/distributed teams need better communication
  • Existing internal tools were fragmented and hard to measure
  • Most companies relied on a messy combo of:
    • HubSpot/Mailchimp
    • Slack
    • intranets
    • ad hoc workarounds

After Flywheel was acquired by WP Engine, Rick saw enterprise communication at a larger scale and realized the market had a real gap.

The Product-Market Fit Journey

This was the centerpiece of the conversation.

The initial wrong turn

Workshop originally tried to build a better intranet:

  • They thought no one liked their intranet
  • They believed better design and UX could improve adoption
  • But they kept hearing a stronger pain point from prospects: email

The signal they ignored

Customers repeatedly said:

  • “Email is our main channel”
  • “We have no visibility into how it performs”
  • “We need to reach employees reliably at scale”

Rick admits the team ignored that signal for 6–9 months, partly due to ego and wanting to build something “more novel” than email.

Why email was actually hard

The enterprise email problem was not about sending prettier emails. It involved:

  • Deliverability and spam filtering
  • Security layers inside enterprise IT environments
  • High-volume distribution
  • Brand consistency
  • Speed of delivery to very large workforces
  • Visibility into engagement

Once they understood the real complexity, the product direction became clear.

The turning point

  • They rebuilt around email in late 2021
  • Sent a message to prospects asking if they wanted the email product
  • Went from 3 customers in 9 months to 10 customers in 30 days
  • That was the moment they knew they had something worth scaling

Go-to-Market and Marketing Strategy

Rick emphasizes that the company spent about a year marketing before really selling.

Main channels they used

  • A weekly newsletter: Happy Monday Club
  • Co-marketing with industry newsletters and community builders
  • A resource library with practical tools, not gated ebooks
  • Webinars, run consistently over time
  • Inbound/SEO content targeting long-tail search demand

Why it worked

Their strategy was to:

  • Solve real problems directly
  • Publish useful assets instead of generic content
  • Build trust and audience before asking for a sale
  • Let the content engine compound over time

Examples of inbound resources

  • Internal comms calendars
  • Benchmark reports
  • Practical templates and guides

Rick’s point: content works when it’s treated like a long-term system, not a one-off campaign.

Mission, Culture, and Leadership Lessons

Rick deliberately started Workshop with a mission before a product.

Mission

  • “Create more Happy Mondays for employees everywhere”

This gave the team a broad but meaningful direction while they figured out the product.

Why that mattered

  • It kept the company aligned during uncertainty
  • It supported multiple initiatives:
    • newsletter
    • webinars
    • conference
    • product development
  • It made the company’s work feel connected to a bigger purpose

Core values that emerged

A key one is “listen to learn.”

  • Customers tell you what the real problem is
  • Ego gets in the way of progress
  • The team learned to stop assuming they knew best

Hiring philosophy

Rick also stresses:

  • Hire optimistic people
  • Protect your A players
  • Hire slowly, fire quickly when necessary
  • Great people want to work with other great people

Pricing and Product Packaging

Workshop uses audience-based pricing, not per-seat pricing.

Pricing structure

  • Based on:
    • number of employees being reached
    • channels used (email, SMS, etc.)

What changed

They briefly experimented with charging for more users, but removed that friction because:

  • It slowed adoption
  • It made procurement harder
  • It reduced time-to-value
  • It hurt expansion within organizations

The goal became simple:

  • Get more departments using the product
  • Make adoption easy
  • Grow through channel expansion, not seat expansion

Founder Advice and Practical Takeaways

Key lessons from Rick’s experience

  • Listen to customers, even when it hurts your original idea
  • Enterprise problems are often more complex than they look
  • You may need a full year of marketing before sales really clicks
  • Product-market fit is often obvious only in hindsight
  • A broad mission can be more useful than a rigid product vision early on

His most important mindset shift

Rick admits that after a successful exit, he assumed some things would be easier the second time. They weren’t.

The lesson:

  • Past success helps with fundraising and credibility
  • It does not eliminate the need to find real customer pain
  • Startup humility still matters

Lightning Round Highlights

Best business advice

  • Protect your A players
  • Great teams need to work with other great people

Favorite book recommendation

  • Shoe Dog by Phil Knight
  • Also mentioned: A Ride of a Lifetime by Bob Iger

Best money spent

  • Quarterly company offsites
  • Expensive, but valuable for alignment in a fast-growing distributed company

Favorite productivity hack

  • Rick uses Claude to turn saved Slack items into email-style to-dos
  • He manages important tasks better in email than in Slack

Life outside work

  • Mostly family time with his nine-year-old daughter
  • He jokes that hobbies have mostly disappeared for now

Bottom Line

Rick Knudtson’s story is a strong example of how customer feedback beats founder assumptions. Workshop nearly died because the team was attached to the wrong product idea. Once they accepted that enterprise email communication was the real problem, growth followed quickly.

The core message of the episode:

  • Don’t ignore the signal customers keep giving you
  • Enterprise communication is a bigger, harder problem than it first appears
  • Consistency in content and inbound marketing can create the foundation for scale
  • Listening carefully can be the difference between no traction and product-market fit