Hitting $5m ARR was not easy
“Hitting $5m ARR was not easy. 3 things we failed & 3 things we nailed. Bridget Harris CEO of YCBM • ycbm.com”
Founder resourceLeader $5m+
Hitting $5m ARR Was Not Easy: 3 Things that Failed
and 3 Things we Nailed
Bridget Harris · YouCanBookMe
Published September 6, 2023About this resource
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Topics covered: Hitting $5m ARR was not easy; Culture; Making Money.
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Culture
“Culture Remote Transparent Profit Share 👌 People and Culture”
Making Money
“Making Money PLG Customers Self Service Profitable 👌”
Product
“Product Features Pricing 😒 Roadmap not Vision Fails and Nails:”
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Bridget Harris Saastr Slide Deck
Bridget Harris is the CEO and co-founder of YouCanBook.me - an online scheduling tool that helps businesses manage their customers and calendars. Bridget is the co-founder of YCBM, launched in 2012. Before then she had a career in parliament, government and politics as an advisor.
- Company revenue
- $5M
- Team size
- 24
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Hitting $5m ARR was not easy
Hitting $5m ARR was not easy. 3 things we failed & 3 things we nailed. Bridget Harris CEO of YCBM • ycbm.com
YCBM in numbers 12 Year Old Company Profitable Since 2017 st Calendar Booking Tool 1
YCBM in numbers 1 million Accounts 20,000 Customers 90 million Bookings all time
Revenue 2023 (£)
Trusted by customers and teams worldwide at
Over the next 30 minutes 3 Fails and 3 Nails Product Making Money People and Culture
12 Years of Fails and Nails 1 Fails and Nails 😒 👌
When loops go viral… 92M+ all time bookings
“There is no such thing as failure. Failure is just life trying to move us in another direction.” — Oprah Winfrey
People & Culture 2 People and Culture
Fails and Nails: People and Culture at YCBM
Fails and Nails: People and Culture at YCBM Culture Remote Transparent Profit Share 👌 We’ve championed culture, profit and internationalism for over a decade and we love it!
Ad hoc management styles led to unintentional mixed messages and lack of clarity Management 😒 Unstructured Founder Dependent Sink or Swim People and Culture at YCBM Fails and Nails:
Management 😒 Unstructured Founder Dependent Sink or Swim Culture Remote Transparent Profit Share 👌 People and Culture
People and Culture Management 😒 Unstructured Founder Dependent Sink or Swim
Introduced EOS / 90 Day Rocks Weekly Exec Meeting Company Bulletin Recordings + AI Transcripts Weekly Scorecard People and Culture Management 😒 Unstructured Founder Dependent Sink or Swim
People and Culture Management 😒 Unstructured Sink or Swim Founder Dependent
Technical Leadership Product Squads Operations Team Ownership People and Culture Management 😒 Unstructured Founder Dependent Sink or Swim
People and Culture Management 😒 Unstructured Founder Dependent Sink or Swim
People and Culture Management 😒 Unstructured Founder Dependent Sink or Swim Talent Sourcing External Coaching and Mentoring Expectations and 1-1s
People and Culture Management 😒 Unstructured Founder Dependent Sink or Swim
Culture Remote Transparent Profit Share 👌 Management 😒 Unstructured Founder Dependent Sink or Swim People and Culture
Culture
Culture Remote Transparent Profit Share 👌 People and Culture
Culture Transparent Profit Share 👌 People and Culture Remote
Culture Remote Transparent Profit Share 👌 People and Culture
Culture Remote Profit Share 👌 People and Culture Transparent
Culture Remote Transparent Profit Share 👌 People and Culture
Culture Remote Transparent 👌 People and Culture Profit Share
Culture Remote Transparent Profit Share 👌 People and Culture 👉🏻 👉🏻 💰 💰 👉🏻 💰 💰 💰 💰
We have changed our internal management, hiring and comms to help us scale Fails and Nails: Management 😒 Unstructured Founder Dependent Sink or Swim
Fails and Nails: Culture Remote Transparent Profit Share 👌 Our cultural north star is our commitment to transparency People and Culture at YCBM
Making Money 3 Making Money
Fails and Nails Making Money
Fails and Nails Bootstrapping ensured we were ruthlessly focussed on product-led growth and a self sustaining profitable business Making Money PLG Customers Self Service Profitable 👌
Marketing Positioning Marketing tactics 360° tracking 😒 Fails and Nails We spread ourselves too thin across a diverse range of customers without a clear message Making Money
Fails and Nails Marketing Positioning Marketing tactics 😒 360° tracking Making Money
Marketing Positioning Marketing tactics 😒 360° tracking PLG Customers Self Service Profitable 👌 Making Money Fails and Nails
Making Money Marketing Positioning Marketing tactics 😒 360° tracking
👌 Marketing Marketing tactics 😒 360° tracking Making Money Positioning
👌 Marketing Positioning Marketing tactics 😒 360° tracking Making Money
👌 Marketing Positioning 😒 360° tracking Making Money Marketing tactics
👌 Marketing 😒 SEO Positioning Marketing Positioning Marketing tactics 😒 360° tracking Making Money
👌 Marketing 😒 SEO Positioning 360o tracking Marketing Positioning Marketing tactics 360o tracking Making Money 😒
Marketing Lack of understanding Short term Low Investment 😒 Marketing Positioning Marketing tactics 😒 360° tracking Making Money PLG Customers Self Service Profitable 👌
Making Money
Making Money PLG Customers Self Service Profitable 👌
PLG Self Service Customers Profitable 👌 Making Money PLG Customers Self Service Profitable 👌
PLG Customers Self Service Profitable 👌 Making Money How it Started…
Making Money How’s your Support Going….? PLG Customers Self Service Profitable 👌
Making Money PLG Self Service Profitable 👌 Customers
Fails and Nails We are proud of building a PLG driven company with over a million people using our product every month PLG Self Service Profitable 👌 Customers
Fails and Nails We are bringing our clinical approach from engineering and operations to the world of marketing Marketing Positioning Marketing tactics 😒 3600 tracking
Product 4 Vision and Change
“I would rather gamble on our vision than make a ‘me, too’ product.” — Steve Jobs
Product Update — 22 June 2022
A Product Vision is not An ‘also-ran’ 👎
A Product Vision is not A roadmap 🙄
A Product Vision is not Refactoring and redesigning 🥱
A Product Vision should be about Solving a real problem. 😎 In a compelling way. Which stays relevant over time.
Fails and Nails:
Fails and Nails: Product Customizable Reliable 👌 Secure Product Features Pricing 😒 Roadmap not Vision
Our day to day had become about fixing YCBM as the problem, not fixing a problem for people Product Features Pricing 😒 Roadmap not Vision Fails and Nails:
Product Customizable Reliable 👌 We have scaled to a product to over a million accounts Secure Fails and Nails:
Product Customizable Reliable 👌 Secure Fails and Nails:
Product Customizable Reliable 👌 Secure Fails and Nails:
Product Customizable Reliable 👌 Secure Fails and Nails:
Fails and Nails: Product Customizable Reliable 👌 Secure
Product Customizable Reliable 👌 Secure Fails and Nails:
Product Customizable Reliable 👌 Secure Fails and Nails: Product Features Pricing 😒 Roadmap not Vision
Product
Product Features Pricing 😒 Roadmap not Vision Fails and Nails:
Our day to day had become about fixing YCBM as the problem, not fixing a problem for people Product Features Pricing 😒 Roadmap not Vision Fails and Nails:
Product Features Pricing 😒 Roadmap not Vision Product
Product Features Pricing 😒 Roadmap not Vision Product
We invested £1.5million and spent 2 years building a better product experience Product Product Features Pricing 😒 Roadmap not Vision
Product Features Pricing 😒 Roadmap not Vision Product
For the first time in 7 years we put prices up, from $10 to $12 per calendar Product Product Features Pricing 😒 Roadmap not Vision
Product Features Pricing Roadmap not Vision Solving a real problem In a compelling way Which stays relevant over time Product 😒
Product And are building a vision where ‘Booker is King’ Product Features Pricing Roadmap not Vision 😒
New views to best suit the use case Building the best Booking Experience of any tool on the market
Building on our success at customization, translations and global reach, we built ‘out of the box’ translated booking pages Languages
We have rethought, rebuilt, and revamped how our booking platform works 6x faster performance, more customization and improved resilience Immediate
Fails and Nails: Product Customizable Reliable 👌 Secure Product Features Pricing 😒 Roadmap not Vision
In the last 30 minutes Fails and Nails Product How do you stay excited about the vision, while building the roadmap day to day? As you scale, the way you manage people and building teams is going to change People and Culture Pure PLG hasn’t been enough to grow long term Making Money Get used to more structure and set clear expectations Marketing has the biggest learning curve for us to adopt Learn the difference
In the last 30 minutes Fails and Nails NAILS ? ? FAILS What are yours? YOU
Get my Bootstrapping Manual! ycbm.com/manual
Onward! Bridget Harris CEO of YCBM • ycbm.com
Building on our success at customization, translations and global reach, we built ‘out of the box’ translated booking pages Languages
Marshall Goldsmith American executive leadership coach and author What Got You Here, Won’t Get You There
People and Culture Take home 250% spread Employee Gross 331% spread Total cost Employer 324% spread