Builders Webinar | Clockwise CEO Matt Martin on the Secrets to PMF
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Hannah from EO team welcomes everyone to the EO Builders webinar featuring founders from EO channel. EO stands for Entrepreneurship and Opportunities, featuring founders and investors worldwide for over a year and a half to provide insights and network to a global audience. Mission: empower individuals with resources to grow as entrepreneurs. Recently launched EO Builders Club, a community for startup founders and potential founders. Scan QR code to join; different tiers. Hosts webinars like this (live streamed today), private weekly webinars with in-depth founder conversations, education programs, online networking. People who resonate with the story resonate with each other.
Special guest: Matt Martin, CEO of Clockwise. Featured on channel twice recently. Clockwise is an AI scheduling and calendar tool used by Uber, Zoom, Atlassian, OpenAI. Raised $45 million Series C in 2022, total funding $80 million. Topic: secrets to product-market fit (PMF) in competitive calendar/scheduling/productivity market.
Matt introduces Clockwise: calendar assistant for you, team, company to get the best schedule possible. Constantly watches schedule, fixes conflicts, opens time for focus and deep work, enables impactful productive work. Works with Netflix, Pinterest, Atlassian, Uber, Chime, other software/tech companies, office workers, large corporations, media, life sciences.
Matt was front-end engineer and engineering manager at RelQ (acquired by Salesforce). At Salesforce, struggled to be proactive; constantly reactive, jumping between meetings/problems/one-on-ones, no time for larger projects. Observed same on team: software engineers, design, marketing lacking time for important work. Intelligent, motivated people want to deliver great work, but schedules conspire against them.
Key insight: issue not lack of time, but time not spent right ways—coordination problem. Meetings scheduled at bad times for participants; Slack distracts during heads-down work. Software good at crunching data, optimizing. Initially optimized calendars automatically using calendar data itself.
Time is the only fair thing—everyone has the same amount; comes down to who spends it best.
Perspective shift: time as shared resource, not personal asset. Colleague requests your time; ask for better time, push back, question necessity.
Prioritization about business impact, changes by stage. Early days (Matt + two co-founders at kitchen table): biggest risk—can algorithmic calendar optimization work on real calendars? Prioritized proving it plausible: get live data from friend, run in-memory experiments.
To get to customers: unblock trust/usage. Sprint to volume of real users for real-world data. Later, prioritize based on usage.
Separate excellent from mediocre execution: focus on what moves business forward.
Journeys differ by market/customer. Stay attuned to customers. Productivity space densely populated. Benefited from strong opinion/edge to find early adopters.
Clockwise general-purpose but initial niche needed. Opinion: everyone needs deep work (different from 15-30 min blocks; Cal Newport's book). Resonated with software engineers—core initial audience. Tailor outreach/materials to them.
Tricky transitioning to broader audience (to discuss later).
Early days: product promise—automatic time gains, low investment/high ROI, set-it-and-forget-it. Customers don't want to talk (not buggy, easy setup).
Methods:
- Email interesting new logos to build relationships; early adopters love influencing product.
- Automated: watch sessions, quantitative data trends, troubleshoot user actions.
- Monitored user sessions: sit with users, watch them use product (rich info; less now due to volume).
Easier to get input on product feelings than general feelings.
PMF ill-defined, amorphous—avoid overthinking as distraction. Pick leading indicator metric (e.g., Rahul's Superhuman blog post).
Key early metrics (retrospective):
- Viral adoption: one user (@ domain.com) invites others same domain? Leads to network growth, selling into businesses.
- Critical feature adoption: Flexible Meetings (mark meeting movable within parameters; unlocks productivity). Measure in first onboarding (push high/fast), overall user base rate. Odds of long-term success rise if used.
- Later: monetization—do they pay and keep paying? (Monetized too late; needed for PLG productivity: growth, adoption, engagement, retention, payment).
User growth acceleration.
Specifics differ by startup; logic key. Clockwise: productivity software, more users = more value (calendar access). Bottom-up (not top-down)—users must trust individually; can't force via leaders.
Must acquire user-by-user, spread organically. Sharing metric tests this: builds to volume without hand-to-hand combat.
Drisk what you're building; shifts over time.
Milestones shift depending on the business model. Hustle culture blends everything together, but it's different for a solo entrepreneur bootstrapping to revenue-positive and profitable, like Basecamp, which has earned a lot for founders without venture capital. Milestones for bootstrapped are more natural and less contorted than for venture-backed companies, where a big milestone is securing the next funding round. Focus on sustaining and powering the business forward. For VC-backed like Clockwise, traction shows if core fundamentals work. For bootstrapping, early revenue matters more than early scale.
Clockwise shifted more towards B2B. Everyone who signs up must use a calendar address associated with a business account; personal Gmail like [email protected] is rejected at signup. This filters for users with scale potential into larger organizations, hurting virality but aligning with revenue from multi-seat users, not single seats.
Over the last five years, buzz around PLG companies like Slack, Dropbox, Atlassian, Notion, Figma. They are productivity software. Advantage: acquire users at scale, use them to acquire more. Undercurrent: easier to just sell the product. PLG creates a good enough product to pull users in, convert to paying, and scale. Figma makes significant money from large licenses like Uber's, not as much from individuals collectively. All PLG companies are fundamentally B2B; revenue engine from larger organizations buying many licenses. Starts looking B2C because anyone can sign up, but scales inside organizations to departmental or company-wide buyers. Tension: acquire users at volume while ensuring it scales for organizational buyers.
PMF definition is ambiguous. Multiple moments at Clockwise felt like PMF: first hockey stick scaling inside an organization; spreading across companies; then adding monetization that worked despite fears. Thought world would be easier post-PMF, but new hurdles emerged: scaling to larger enterprises, zero interest rates ending, budgets tightening, mild recession, layoffs. PMF benchmark shifted as businesses got stricter on spending.
PMF process: stay in touch with customer expectations, which shift due to market corrections, competitors, incumbents entering space. Constantly watch and adjust to maintain fit. Expands as business grows to new users/audiences, building on core thesis, finding new pockets.
Scaling to enterprise requires balancing end-user delight with buyer needs. Salesforce example: not most loved by end users (clunky, hard to enter data, startups built to ease it), but successful selling to sales leaders or central provisioning with robust features. PLG acquisition via product means always improving end-user experience. Product builder prefers this over sales/marketing strength.
Tricky at enterprise scale: keep end users happy for acquisition/retention while layering enterprise value. End-user value should align with enterprise value, making users better employees. Can't just add SSO/compliance; think about enterprise buyer needs (easy deploy, secure, team coordination, productivity gains). May require whole new product areas.
Shift to enterprise hasn't fundamentally changed team organization. Not at scale for dedicated enterprise product squad yet; build cohesively against priorities, sometimes enterprise-focused. Biggest change is team scale: add leadership level, functional experts. Founder CEO shifts from direct prioritization with engineers to managing product/engineering leaders, sales leaders. Job becomes setting vision, caring for leadership team, ensuring culture.
Founder CEOs continuously do jobs without credentials: early selling without sales experience, then managing sales leaders without team organization experience. Engaging and exciting.
Clockwise started late 2016, off ground 2017, private beta to figure mechanics, public ~2018-2019, monetized first in 2020 (three years in). Worked, quickly reached sizable recurring revenue, but waited too long. Weird incentives without monetization: build features for non-paying users. Paying users are best filter for those who matter, ascribe value. Time on non-converting users wastes precious startup resources.
Incorporate monetization early for cleaner learnings, fewer wasted cycles. Early days prioritized product/engineering reliability: complex under hood (Google Calendar integration, millions of events, schedules must be perfect—errors like time zones lead to immediate firing). Felt premature to charge before scaling right. Retrospect: fear-based; high bar as engineer/product founder. Take leap: if no one pays, not ready yet. Should have had lightweight 'pay if you want' early for power user signal, even if not meaningful revenue.
Backed by top VCs: Accel Partners (Steve Loughlin), Greylock Partners (John Lilly, invested in Figma, Instagram; now retired but on board), B Capital (AJ Edelman). Seasoned, rational, not fear-prone. Era of PLG excitement, low rates, growth-at-all-costs focus allowed delaying monetization. VCs had faith in scaling value to enable payment. Riskier bet today with cash flow focus.
From Day Zero (or negative 3), always planned venture-backed for large impact potential. Coming from startup acquired by Salesforce with good jobs, wanted big swing. Bootstrapping possible but hard for rapid scale investment. Needed time/money to develop product, scale users upfront.
Started casual investor conversations from day one.
Started having casual conversations with investors from day one.
Many product builders battle with premium pricing strategies. Features that drive high growth should usually be free.
Clockwise Pricing Structure: Anchor in the overall value and vision of the product. Ideally, massive drivers of value are behind the paywall, while massive drivers of user acquisition are free. This isn't always possible.
Slack Example: Deep value is as the central place for messaging, conversation history, integrations. Scale requires adoption first. Features like Slack Connect should be free to incentivize connecting and bringing in more users. Slack has struggled to draw clear monetization lines around the core conversation engine.
Look across feature set, inform with user data on usage. Ultimately, it's a gut call. Evaluate: Is the most important value driver spreading the product (growth mode)? Put it in the free plan as marketing investment, foregoing revenue. For core value drivers that take time to adopt, use usage-based thresholds to hook users and push conversion. More art than science.
Discrete value of the business of this feature and where it should exist in the plans.
[Light-hearted interruption: Cracking a window due to sun making the room a sauna.]
MTA's Question (full stack developer): Suggestions to nail the interview process at Clockwise?
Perceptible shift in job market: More candidates due to software recession, layoffs, less hiring. Stand out beyond skill set bar (engineering interviews have a bar to clear).
Advice:
- Identify your unique asset: Exceedingly entrepreneurial, love building, calendars/productivity passion?
- Tell that story.
- Bonus: LinkedIn connections to punch through noise (to Matt or engineering leader).
First three hires post-seed round: All prior colleagues. Luxury not everyone has.
Early days: Seek people who can move fast, whom you trust and who trust you to take a leap—often prior relationships. Avoid monoculture for better products (diversity yields insights, especially for productivity tools building for the world).
Dogfood the product at 100%. Use Clockwise links (better than Calendly). One-on-ones as flexible meetings with range settings.
Key Insights:
- Reduce fragmented time: Avoid back-to-back meetings without breaks; condense meetings (e.g., 9am then 1pm then 3pm is suboptimal).
- Condense into like-minded zones (CEO buckets leadership one-on-ones on one day, staff meeting after).
- Clockwise enables swapping within ranges.
- Proactive deep work time: Weekly beat (Friday/Sunday/Monday) to plan priorities, check calendar realistically, block focus time (not per task, but total hours needed for 15-20 tasks).
Be intentional about time, respectful of others', coordinate to avoid fragmentation.
Team: Completely remote, ~55 people across US. Pre-pandemic: 110% office advocate (miss energy). Now: Trade-offs—hiring talent nationwide outweighs; bring people together for energy (not full replacement).
Demetri: Building online education for emerging markets (India, Brazil) kids to study in UK/US/Canada schools. Downturn in sector; considering pivot.
Love the space. Even online credentials boost resumes (people skim LinkedIn/resumes; online class at school can get foot in door).
Clockwise: No major pivots. Early: Thought outside calendar (website), landed on Chrome extension to augment tools, then web app—iterations, not fundamental change.
Pivot Advice: Hard, especially at scale (few large companies succeed). Pivot when small. Leverage learnings on pain points/value; talk to community to find unique angle.
Product has good traction; need technical co-founder for selling.
Trade-offs:
- Every bit of traction before investors/employees is huge.
- Hiring now: Pay salary/equity (dilutes you), or fundraise (more dilution with less traction).
- Solo founder pain is deep; partner/technical speed beneficial.
Recommendation: Focus on sales for traction (e.g., next 6 months) to make hiring easier/better candidates. But if awesome buddy co-founder you vibe with, do it now. Weigh focus/distraction.
Sources: Hacker News, Product Hunt, X/Twitter (annoying ads but useful), community events. Tune to buyers (end users, IT managers, productivity suite runners).
Founder psychology: Past guilt over not reading business books. Now at peace focusing on interests: AI (reading papers, YouTube; building in it), home automation.
Balance forced (ecosystem/buyers) with genuine interests.
Varies by day. Personal/internal work: Reflect on who you are, what matters.
Dirty secret: Work hard and fail, or cruise and succeed—luck/timing huge.
Community observation: Some mediocre founders get rich; brilliant ones fail.
Maturity: Run your journey your way. Energy in = energy out. Stressed/anxious? Live it daily (brutal). Focus on controllable, company direction, loves (great people, product). Feel lucky to make software daily.
Trust what you care about/believe/control.
Clockwise does some, not main source.
Key: Add value, not sales pitch (falls on deaf ears). Leverage founder authenticity/customization.
Bad: "Tool increases productivity 10x." Good: Seek advice (e.g., "Advice on scaling eng org/productivity?")—tailor to audience, hook with value.
"Your workday your way."
Test, iterate endlessly; never done. Clever ideas often tank conversion. Be humble. (Not Matt's forte; hired experts.)
Thought about it: Internal "capacity planner" project (Sprint tool)—killed it.
Tension: General-purpose vs. deep niche. Stay true to audience.
Too niche (software eng Sprints). Better: Augment outsiders via API/Jira integration (push capacity data). Generic API across tools > custom interface (not core to productivity software).
AI: Foundational tech improving. Unlike crypto (saw tech, no use case), AI has use cases. Problem: Don't know great AI UX yet.
ChatGPT: Generic, mass market. GitHub Copilot: Nailed defined use case. Many others (summarize text, transcripts, translations)—not harnessing well. Excited for creativity unlocked.
Michael Bloomberg (bootstrapped, cashed out prior firm for capital): "Why give away company to VCs?"
Rational if possible. But: Need capital to start; opportunity cost of time (VC enables faster scaling). Weigh variables: Capital needs, speed value, bootstrap feasibility.
If on own income: Do it.
Productivity tricky: Soft ROI.
Consumer: Dead end—people terrible at valuing time, won't pay. No successful pure consumer productivity businesses.
B2B: Soft ROI (harder to trace vs. sales/marketing tools). Strong personal opinions ("glove problem"—fits me perfectly, not you; e.g., favorite email clients).
Calendly Discussion: Arguably B2B (business context, ROI = more business).
Be sober about end-state market fit. Love vision? Great, but market pull > willpower/work ethic/product quality. Crappiest product wins if market salivates.
Too many fall in love with vision/technology, not validating market need/desire.
[Wrap-up: Thanks, join Builders Club webinars weekly.]
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