YCBM in numbers
“Calendar Booking Tool”
Founder resourceLeader $5m+
Hitting $5m ARR Was Not Easy: 3 Things that Failed
Three things that failed and three that worked across product, making money, and people and culture at a profitable 12-year-old company
Bridget Harris · YouCanBookMe
Published September 6, 2023About this resource
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What you’ll learn
YouCanBookMe describes 12 years of profitable operations. The deck covers hiring and coaching practices, monthly product use, a product roadmap setback, and differences in employee compensation costs.
Read the source passagesKey moments
Find the ideas you need and go straight to the source.
People and Culture
“External Coaching and Mentoring”
Fails and Nails
“We are proud of building a PLG driven company with over a million people using our product every month”
Product
“Roadmap not Vision”
Compensation varies across employee costs
“People and Culture”
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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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92 passages
Introduction
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Hitting $5m ARR was not easy. 3 things we failed & 3 things we nailed. Bridget Harris CEO of YCBM • ycbm.com
YCBM in numbers
A decade of profitable operations
The company describes itself as a calendar booking tool, in business for 12 years and profitable since 2017.
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YCBM in numbers 12 Year Old Company Profitable Since 2017 st Calendar Booking Tool 1
Usage spans accounts, customers, and bookings
The company reports 1 million accounts, 20,000 customers, and 90 million bookings to date.
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YCBM in numbers 1 million Accounts 20,000 Customers 90 million Bookings all time
Revenue accelerated over time
The annual revenue curve rises gradually at first, then climbs more quickly through the later years, reaching its highest point at the right edge.
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Revenue 2023 (£)
Recognizable teams use the product
A set of customer logos signals adoption across consumer services, commerce, transportation, reviews, and technology.
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Trusted by customers and teams worldwide at
Customers span the satisfaction map
The logo map organizes customer companies by satisfaction and performance, with YCBM marked in the upper-right leaders area.
Three parts structure the talk
The talk will examine failures and successes in people and culture, making money, and product.
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Over the next 30 minutes 3 Fails and 3 Nails Product Making Money People and Culture
The talk reviews a dozen years
This section looks back at the company’s failures and successes across 12 years.
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12 Years of Fails and Nails 1 Fails and Nails 😒 👌
Bookings grew as the loops spread
The bookings chart grows from a low baseline into a much steeper curve, alongside a headline of 92M+ lifetime bookings.
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When loops go viral… 92M+ all time bookings
A reaction image frames a setback
A comic scene and its caption convey a disappointed response, setting up the talk’s discussion of failures.
Failure can redirect progress
The displayed quote reframes failure as life moving a person toward a different direction.
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“There is no such thing as failure. Failure is just life trying to move us in another direction.” — Oprah Winfrey
People and culture comes first
This section introduces the people and culture portion of the failures-and-successes review.
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People & Culture 2 People and Culture
People and culture at YCBM
The section will examine what went wrong and what worked in the company’s approach to people and culture.
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Fails and Nails: People and Culture at YCBM
Remote work and profit sharing are strengths
The company presents remote work, transparency, and profit sharing as cultural practices it has championed for more than a decade.
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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 caused confusion
Unstructured, founder-dependent management and sink-or-swim expectations led to mixed messages and unclear direction.
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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 struggled while culture held
The comparison pairs unstructured, founder-dependent management with remote, transparent, profit-sharing culture.
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Management 😒 Unstructured Founder Dependent Sink or Swim Culture Remote Transparent Profit Share 👌 People and Culture
Management relied on the founder
The management list highlights unstructured work, dependence on the founder, and sink-or-swim expectations as problems.
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People and Culture Management 😒 Unstructured Founder Dependent Sink or Swim
Operating rhythms add structure
The proposed management practices include EOS and 90-day goals, weekly executive meetings, company updates, recorded meetings with AI transcripts, and a weekly scorecard.
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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
Founder dependence is singled out
This build emphasizes founder-dependent management as a specific weakness within the broader management problem.
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People and Culture Management 😒 Unstructured Sink or Swim Founder Dependent
Teams can own clear responsibilities
Technical leadership, product squads, and an operations team are presented as ways to distribute ownership.
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Technical Leadership Product Squads Operations Team Ownership People and Culture Management 😒 Unstructured Founder Dependent Sink or Swim
Sink-or-swim management is a risk
The highlighted management failure is leaving people to figure things out without sufficient support.
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People and Culture Management 😒 Unstructured Founder Dependent Sink or Swim
People and Culture
Hiring and coaching support employees
Talent sourcing, external coaching and mentoring, and clear expectations with regular one-to-ones are listed as management practices.
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People and Culture Management 😒 Unstructured Founder Dependent Sink or Swim Talent Sourcing External Coaching and Mentoring Expectations and 1-1s
Management problems share a pattern
The list groups management challenges around weak structure, founder dependence, and sink-or-swim expectations.
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People and Culture Management 😒 Unstructured Founder Dependent Sink or Swim
The comparison turns toward culture
The management list fades as the culture list comes forward, shifting attention to the company’s cultural strengths.
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Culture Remote Transparent Profit Share 👌 Management 😒 Unstructured Founder Dependent Sink or Swim People and Culture
Three cultural practices stand out
Remote work, transparency, and profit sharing form the company’s stated culture strengths.
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Culture Remote Transparent Profit Share 👌 People and Culture
Remote work is one cultural strength
The build emphasizes remote work within the company’s three-part culture framework.
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Culture Transparent Profit Share 👌 People and Culture Remote
Team locations balance flexibility and ties
The country map positions locations against relationship security and flexibility or cost, illustrating tradeoffs in where a remote team is based.
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Culture Remote Transparent Profit Share 👌 People and Culture
Culture is expressed through shared values
A collage of value posters puts commitment, curiosity, problem solving, simplicity, and challenge at the center of the culture discussion.
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Culture Remote Profit Share 👌 People and Culture Transparent
Transparency is a stated cultural value
The build highlights transparency beside remote work and profit sharing, with a photo of colleagues gathered around a table.
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Culture Remote Transparent Profit Share 👌 People and Culture
Transparency joins the culture framework
Remote work, transparency, and profit sharing are presented together as the company’s culture strengths.
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Culture Remote Transparent 👌 People and Culture Profit Share
Profit sharing follows a points schedule
The employee table increases points by 0.25 each quarter, reaching 4 points in quarter 16.
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Culture Remote Transparent Profit Share 👌 People and Culture 👉🏻 👉🏻 💰 💰 👉🏻 💰 💰 💰 💰
Internal practices changed to support scale
The company says it changed management, hiring, and communications to help the business scale.
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We have changed our internal management, hiring and comms to help us scale Fails and Nails: Management 😒 Unstructured Founder Dependent Sink or Swim
Transparency guides the culture
The company describes transparency as its cultural north star.
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Fails and Nails: Culture Remote Transparent Profit Share 👌 Our cultural north star is our commitment to transparency People and Culture at YCBM
The talk turns to making money
This section introduces the financial and business model portion of the failures-and-successes review.
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Making Money 3 Making Money
Making money at YCBM
The next section examines what worked and failed in building a sustainable business.
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Fails and Nails Making Money
Bootstrapping focused the business on PLG
The company says bootstrapping kept its focus on product-led growth, self-service customers, and a profitable business.
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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 👌
Broad marketing diluted the message
The company spread effort across varied customers and marketing tactics without clear positioning.
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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
A reaction image follows marketing sprawl
A confused reaction image accompanies the broad marketing checklist, reinforcing the difficulty of a scattered approach.
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Fails and Nails Marketing Positioning Marketing tactics 😒 360° tracking Making Money
Marketing and product-led growth are compared
The framework contrasts positioning, marketing tactics, and tracking with product-led growth, self-service customers, and profitability.
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Marketing Positioning Marketing tactics 😒 360° tracking PLG Customers Self Service Profitable 👌 Making Money Fails and Nails
Marketing was a source of failure
This build isolates marketing as the failing area within the making-money section.
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Making Money Marketing Positioning Marketing tactics 😒 360° tracking
Positioning is the first marketing question
The build highlights positioning and pairs it with a book about making products distinct and understandable to customers.
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👌 Marketing Marketing tactics 😒 360° tracking Making Money Positioning
The product promise makes positioning visible
A booking-tool homepage illustrates how product positioning appears in a customer-facing message and interface.
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👌 Marketing Positioning Marketing tactics 😒 360° tracking Making Money
Marketing tactics can be compared externally
A software directory screenshot shows how products are grouped and compared across categories and capabilities.
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👌 Marketing Positioning 😒 360° tracking Making Money Marketing tactics
Search activity is measurable over time
A search analytics dashboard displays changing impressions and clicks, with a fluctuating upward trend in the later period.
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👌 Marketing 😒 SEO Positioning Marketing Positioning Marketing tactics 😒 360° tracking Making Money
Tracking connects marketing data sources
The diagram routes social sources, a website, and a CRM into an analytics platform, then into reporting tools.
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👌 Marketing 😒 SEO Positioning 360o tracking Marketing Positioning Marketing tactics 360o tracking Making Money 😒
Marketing needed depth and sustained effort
The slide names limited understanding, short-term thinking, and low investment as marketing weaknesses before turning toward product-led growth.
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Marketing Lack of understanding Short term Low Investment 😒 Marketing Positioning Marketing tactics 😒 360° tracking Making Money PLG Customers Self Service Profitable 👌
Product-led growth supports profitability
The company frames product-led growth around serving customers, self-service, and profitability.
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Making Money PLG Customers Self Service Profitable 👌
Customer adoption is the next PLG focus
A sequence of figures climbs a set of steps as the framework highlights customers, suggesting progress toward broader adoption.
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PLG Self Service Customers Profitable 👌 Making Money PLG Customers Self Service Profitable 👌
Earlier products built usage over time
The comparison traces three product launches through successive account, activity, and booking milestones.
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PLG Customers Self Service Profitable 👌 Making Money How it Started…
Self-service support gives customers options
A support page offers webinars, help documents, a community forum, and contact support.
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Making Money How’s your Support Going….? PLG Customers Self Service Profitable 👌
Three operating stacks connect to profit
The diagram groups company functions, people practices, and business activities into separate stacks, each building toward profit.
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Making Money PLG Self Service Profitable 👌 Customers
Fails and Nails
Monthly product use supports the PLG story
The company says more than a million people use its product each month.
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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
Marketing is adopting a clinical approach
The company says it is applying the methodical approach used in engineering and operations to marketing.
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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 vision and change
This section introduces the product portion of the failures-and-successes review.
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Product 4 Vision and Change
Choose a distinct product vision
The quote argues for betting on a clear vision instead of building a copycat product.
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“I would rather gamble on our vision than make a ‘me, too’ product.” — Steve Jobs
Scheduling products compete on experience
A collage of booking and scheduling product pages shows varied approaches to meetings, calendars, and online scheduling.
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Product Update — 22 June 2022
A vision should distinguish the product
The slide argues that a product vision should not simply follow category conventions, alongside examples of scheduling pages.
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A Product Vision is not An ‘also-ran’ 👎
A roadmap is not a product vision
The timeline lays out work across multiple initiatives, illustrating that a roadmap organizes projects rather than defining the product’s purpose.
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A Product Vision is not A roadmap 🙄
Refactoring alone is not a vision
The slide distinguishes a lasting product direction from redesigning interfaces or refactoring the existing experience.
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A Product Vision is not Refactoring and redesigning 🥱
A vision solves an enduring real problem
The slide defines product vision through solving a real problem compellingly in a way that stays relevant over time.
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A Product Vision should be about Solving a real problem. 😎 In a compelling way. Which stays relevant over time.
Product failures and successes
This transition brings the discussion back to the product failures-and-successes framework.
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Fails and Nails:
Product quality needs more than a roadmap
The comparison sets customizability, security, and reliability against a focus on features, pricing, and roadmaps without a vision.
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Fails and Nails: Product Customizable Reliable 👌 Secure Product Features Pricing 😒 Roadmap not Vision
The team focused on fixing itself
The company says day-to-day work had become about fixing YCBM rather than solving a problem for customers.
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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:
A million accounts tested the product
The company says its product has scaled to over a million accounts, with customizability, reliability, and security as its strengths.
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Product Customizable Reliable 👌 We have scaled to a product to over a million accounts Secure Fails and Nails:
A quiet transition in the product section
This mostly blank frame separates the product-strength sequence without adding another takeaway.
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Product Customizable Reliable 👌 Secure Fails and Nails:
Customers value flexible booking flows
A customer comment praises the ability to create booking flows and communications that fit the customer’s voice, illustrated with confirmation and reminder examples.
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Product Customizable Reliable 👌 Secure Fails and Nails:
Security is supported by standards and privacy
Security logos and a GDPR badge illustrate the certifications and privacy commitments associated with this product strength.
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Product Customizable Reliable 👌 Secure Fails and Nails:
Bookings show long-term product usage
The slide reports 92,029,068 bookings all time as evidence of sustained use.
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Fails and Nails: Product Customizable Reliable 👌 Secure
Reliability completes the product strengths
The build emphasizes reliability alongside customizability and security.
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Product Customizable Reliable 👌 Secure Fails and Nails:
A roadmap can crowd out product vision
The comparison returns to feature and pricing work and a roadmap, with an arrow toward the missing product vision.
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Product Customizable Reliable 👌 Secure Fails and Nails: Product Features Pricing 😒 Roadmap not Vision
Features and pricing are not the whole vision
The failure list isolates features, pricing, and roadmap focus as an incomplete basis for product direction.
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Product Features Pricing 😒 Roadmap not Vision Fails and Nails:
Solve customer problems, not product symptoms
The company repeats that its work had focused on fixing YCBM instead of solving a problem for people.
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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:
A reaction image marks a product frustration
A comic reaction image accompanies the feature-focused product failure, conveying frustration with that approach.
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Product Features Pricing 😒 Roadmap not Vision Product
Product
Feature work had become the focus
The build highlights features in the product failure list, with a reaction image reinforcing the frustration.
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Product Features Pricing 😒 Roadmap not Vision Product
A major rebuild took time and investment
The company says it invested £1.5million and spent 2 years building a better product experience.
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We invested £1.5million and spent 2 years building a better product experience Product Product Features Pricing 😒 Roadmap not Vision
Pricing changes required customer communication
A product announcement page introduces a pricing update and explains the change to customers.
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Product Features Pricing 😒 Roadmap not Vision Product
Prices rose after seven years
The company says it increased the price per calendar from $10 to $12 after seven years.
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For the first time in 7 years we put prices up, from $10 to $12 per calendar Product Product Features Pricing 😒 Roadmap not Vision
A product vision combines three tests
The recap says a vision solves a real problem, does so compellingly, and remains relevant over time.
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Product Features Pricing Roadmap not Vision Solving a real problem In a compelling way Which stays relevant over time Product 😒
The vision puts booking at the center
The company describes a direction where booking is the defining product priority.
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Product And are building a vision where ‘Booker is King’ Product Features Pricing Roadmap not Vision 😒
Booking views should fit each use case
A mobile scheduling interface illustrates a booking experience designed around the customer’s situation.
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New views to best suit the use case Building the best Booking Experience of any tool on the market
Translated pages extend global reach
The company says it built translated booking pages on top of its customization and international reach; localized calendar interfaces illustrate the result.
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Building on our success at customization, translations and global reach, we built ‘out of the box’ translated booking pages Languages
A rebuilt platform improved performance
The company says the redesigned booking platform delivers 6x faster performance, more customization, and improved resilience.
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We have rethought, rebuilt, and revamped how our booking platform works 6x faster performance, more customization and improved resilience Immediate
Product strengths contrast with old priorities
The framework again contrasts customization, security, and reliability with features, pricing, and roadmap focus.
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Fails and Nails: Product Customizable Reliable 👌 Secure Product Features Pricing 😒 Roadmap not Vision
Three lessons summarize the talk
The recap connects changing people management, learning product-led growth, and balancing vision with the daily roadmap.
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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
Audience members are asked to reflect
The closing exercise asks the audience to identify their own failures and successes.
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In the last 30 minutes Fails and Nails NAILS ? ? FAILS What are yours? YOU
A bootstrapping manual is offered
A QR code invites the audience to get the speaker’s bootstrapping manual.
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Get my Bootstrapping Manual! ycbm.com/manual
The speaker leaves the audience with momentum
The final speaker card closes with an encouraging call to continue forward.
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Onward! Bridget Harris CEO of YCBM • ycbm.com
Localized booking pages show the language options
This continued build shows several localized booking-page interfaces, extending the examples of translated scheduling.
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Building on our success at customization, translations and global reach, we built ‘out of the box’ translated booking pages Languages
Past success may not predict future success
The featured book title suggests that the habits that enabled earlier success may need to change to reach the next level.
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Marshall Goldsmith American executive leadership coach and author What Got You Here, Won’t Get You There
A quiet transition frame
This mostly blank frame pauses the sequence and adds no separate takeaway.
Compensation varies across employee costs
Compensation varies across employee costs
The chart compares spreads in take-home pay, employee gross pay, and total employer cost, reporting 250%, 331%, and 324% respectively.
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People and Culture Take home 250% spread Employee Gross 331% spread Total cost Employer 324% spread
The presentation ends on a blank frame
A minimal final frame closes the deck without adding another message.