Visual summary of operating lessons from Harry Glaser.

Lessons from Harry Glaser

Harry Glaser co-founded Periscope Data and served as CEO until its $130 million acquisition by Sisense. He pairs a practical approach to building data tools with unusually candid writing on the psychological toll of being a founder. This profile gathers his advice for designing data infrastructure, scaling early-stage teams, and managing periods of high growth.

Part 1: Founder Psychology and Survival

  1. On Founder Validation: "The biggest surprise first-time founders experience is the total lack of external validation in their day-to-day professional lives, and the root cause of giving up is the inability to cope with it." — Source: Harry Glaser's Blog
  2. On Winning: "Nobody cares. Just win. You'll be judged by the outcome alone, and I fundamentally don't care if you won by tripping and falling over the finish line, as long as you won." — Source: Harry Glaser's Blog
  3. On Resilience: "In my experience, the biggest cause of death in early stage startups is founders giving up." — Source: Harry Glaser's Blog
  4. On Managing Energy: "The days are long but the years are short; pacing yourself is a requirement for long-term survival in any startup." — Source: Harry Glaser's Blog
  5. On The Reality of Growth: "Growth masks a lot of internal problems, but when growth slows down, every minor cultural crack suddenly becomes a wide chasm." — Source: SaaStr Podcast
  6. On Founder Mode: "Founders have a specific operating mode that requires deep context across all parts of the business, a mode that hired executives often struggle to replicate." — Source: Harry Glaser's Blog
  7. On Handling Rejection: "You have to build a psychological callous to rejection, because early on, everyone—investors, candidates, and customers—will tell you no." — Source: AppSelekt
  8. On Delegation: "The hardest transition for a technical founder is realizing that writing code is no longer the most impactful use of your time." — Source: Software Engineering Daily
  9. On Decision Fatigue: "Make fewer decisions, but make them count. Save your mental energy for the inflection points that actually change the trajectory of the business." — Source: Harry Glaser's Blog
  10. On Self-Awareness: "Glaser argues that founders need to separate their self-worth from the company's growth rate and get their own head, habits, and health back in order before they can steady the business." — Reference: When the growth slows

Part 2: Hiring and Team Building

  1. On Hiring Executives: "When hiring an executive, you are buying a playbook. Make sure you actually want the playbook they are selling before you bring them on board." — Source: Harry Glaser's Blog
  2. On Building the Initial Team: "Your first ten hires dictate the culture for the next hundred. If you compromise on quality early, you will never recover." — Source: SaaStr Podcast
  3. On Firing: "Firing is a failure of the hiring process, but keeping a bad fit is a failure of leadership." — Source: Medium
  4. On Co-Founders: "Start with the right co-pilot. Your relationship with your co-founder is the foundation of the entire company, and any cracks there will eventually bring the whole structure down." — Source: AppSelekt
  5. On Interviewing: "Do not hire people who cannot clearly explain the impact of their past work. If they don't know why what they did mattered, they won't know why their work here matters." — Source: Harry Glaser's Blog
  6. On Managing Managers: "Transitioning from managing individual contributors to managing managers requires letting go of the details and focusing entirely on outcomes and coaching." — Source: SaaStr Podcast
  7. On Compensation: "Pay fairly and transparently. Inequities in compensation are a ticking time bomb for team morale." — Source: Medium
  8. On Employee Retention: "People leave because they stop learning or they stop believing in the leadership. It is your job to ensure neither happens." — Source: AppSelekt
  9. On Promoting from Within: "Internal promotions are great for morale, but you have to recognize when a role has outgrown an employee's current capabilities and bring in external experience." — Source: Harry Glaser's Blog
  10. On Reference Checks: "The best signal in a reference check is what the person leaves out. Listen carefully to the hesitations and the silence." — Source: Medium

Part 3: Data Analytics and Infrastructure

  1. On Data Access: "The core problem in analytics isn't the tooling; it's that the people who have the questions often don't have direct access to the data." — Source: Software Engineering Daily
  2. On SQL as a Standard: "SQL remains the lingua franca of data. Despite all the new tools, if you want to understand data, you need to speak SQL." — Source: Periscope Data Blog
  3. On the Modern Data Stack: "The modern data stack is less about a specific set of tools and more about the philosophy of decoupling storage, processing, and visualization." — Source: Software Engineering Daily
  4. On Dashboards: "A dashboard is only useful if it drives a decision. If a metric goes up or down and nobody changes their behavior, that metric shouldn't be on the dashboard." — Source: Solutions Review
  5. On Data Culture: "A true data-driven culture starts at the top. If the CEO makes decisions based on gut feeling despite the data, the rest of the company will do the same." — Source: SaaStr Podcast
  6. On Speed of Analysis: "Time-to-insight is the defining metric for an analytics team. An okay answer today is better than a perfect answer next week." — Source: Periscope Data Blog
  7. On Data Silos: "Silos kill data utility. The value of data compounds when it is joined across different departments and systems." — Source: Solutions Review
  8. On Self-Serve Analytics: "True self-serve analytics is a myth for complex questions, but a necessity for basic reporting. Know which one you are building for." — Source: Software Engineering Daily
  9. On Data Engineering: "Data engineers should spend their time building scalable pipelines, not fixing broken queries for the marketing team." — Source: Medium
  10. On Visualizing Data: "The goal of data visualization is to remove cognitive load. The insight should be obvious within three seconds of looking at the chart." — Source: Periscope Data Blog

Part 4: Sales and Go-to-Market Strategy

  1. On Non-Technical Sales: "You can build and train a non-technical sales team to sell technical products if you provide them with clear, repeatable playbooks and deep product support." — Source: SaaStr Podcast
  2. On Sales Compensation: "Your sales comp plan dictates your company's strategy. If you want a specific outcome, you have to directly tie the commission to that outcome." — Source: SaaStr Podcast
  3. On Product-Led Growth: "Product-led growth works best when the time-to-value is nearly zero. If it takes three weeks to see the benefit, you need a sales team." — Source: Medium
  4. On Customer Objections: "An objection is just a request for more information. Treat it as an opportunity to educate rather than an argument to win." — Source: SaaStr Podcast
  5. On Pricing: "Pricing is the most powerful and underutilized lever in a startup. Never set it and forget it; constantly test what the market will bear." — Source: AppSelekt
  6. On Founder-Led Sales: "In the early days, the founder must do the selling. Only the founder has the authority to make product commitments on the fly to close an important deal." — Source: Harry Glaser's Blog
  7. On Sales Engineering: "A great sales engineer bridges the gap between the customer's technical reality and the salesperson's value proposition." — Source: SaaStr Podcast
  8. On Churn: "Churn is a trailing indicator. By the time a customer cancels, the failure happened months ago." — Source: Medium
  9. On Ideal Customer Profiles: "Defining who you are not selling to is just as important as defining who your ideal customer is." — Source: AppSelekt

Part 5: Diversity, Inclusion, and Culture

  1. On Inclusion First: "From my perspective a lot of companies get it wrong when they put diversity before inclusion. I believe that if you focus on building an inclusive company then diversity will happen as a result." — Source: Scribd
  2. On Measuring Diversity: "You manage what you measure. If you want a diverse team, you have to track diversity metrics at every stage of the hiring pipeline." — Source: SaaStr Podcast
  3. On Culture Fit vs. Add: "Stop hiring for culture fit. Hire for culture add. You want people who bring something new to the table, not people who replicate what you already have." — Source: Medium
  4. On Unconscious Bias: "Every process has bias. The goal is not to eliminate it entirely, which is impossible, but to build systems that actively counteract it." — Source: SaaStr Podcast
  5. On Remote Work Culture: "Remote work forces you to make your culture explicit. You can no longer rely on osmotic communication around the office." — Source: Harry Glaser's Blog
  6. On Transparency: "Transparency builds trust, but radical transparency requires context. Data without context causes panic." — Source: Medium
  7. On Core Values: "Your company values are not what you write on the wall; they are the behaviors you reward, promote, and fire for." — Source: Harry Glaser's Blog
  8. On Psychological Safety: "If people are afraid to point out when the CEO is wrong, you have failed at building a healthy culture." — Source: SaaStr Podcast
  9. On Employee Resource Groups: "ERGs are vital for inclusion, but they must be supported with real budget and executive sponsorship to be effective." — Source: Medium

Part 6: Acquisitions and M&A

  1. On Selling a Company: "Selling a company is an emotional rollercoaster. You have to detach your personal identity from the entity you built." — Source: SaaStr Podcast
  2. On M&A Strategy: "Acquisitions rarely work out if the cultural alignment is ignored in favor of financial synergies." — Source: SaaStr Podcast
  3. On Integration: "The hardest part of an acquisition isn't the deal; it's the integration. Merging two engineering cultures is notoriously difficult." — Source: Medium
  4. On Deal Velocity: "Time kills all deals. If an acquisition discussion is dragging out, the probability of it closing drops exponentially." — Source: SaaStr Podcast
  5. On Post-Acquisition Roles: "Founders often struggle post-acquisition because they go from having complete control to being a middle manager in a larger machine." — Source: Harry Glaser's Blog
  6. On Due Diligence: "Due diligence will uncover every shortcut you ever took. Build your company from day one as if someone is going to audit it tomorrow." — Source: Medium
  7. On Earnouts: "Earnouts are structured to align incentives, but they often lead to misaligned priorities if the parent company changes strategy." — Source: SaaStr Podcast
  8. On Communicating with the Team: "During an M&A process, say nothing until the ink is dry, but once it is, over-communicate the rationale to your team." — Source: Medium
  9. On Legacy: "Your legacy isn't the exit price; it's what the people you hired go on to do next." — Source: Harry Glaser's Blog

Part 7: AI, Machine Learning, and Engineering

  1. On AI Practicality: "Glaser's practical AI focus is concrete: build agents that handle business data analysis and data science work for customers instead of chasing abstract sci-fi narratives." — Reference: Harry Glaser about page
  2. On AI Conscience: "In his Data Driven NYC talk, Glaser warns that AI builders need to think harder about the moral and ethical implications of the software they ship and resist easy ethical compromises." — Reference: The Conscience of AI talk
  3. On Deploying Models: "Building a machine learning model is the easy part. Deploying it into production and maintaining its accuracy over time is where companies fail." — Source: Modelbit Blog
  4. On Technical Debt: "Technical debt is a tool. Borrow heavily to find product-market fit, but pay it back aggressively once you start scaling." — Source: Harry Glaser's Blog
  5. On Data Science Workflow: "Data scientists should not have to learn Kubernetes to deploy a model. Infrastructure should be abstracted away." — Source: Modelbit Blog
  6. On AI Agents: "AI agents for data analysis will eventually handle the rote querying, shifting the human role to defining the strategic questions." — Source: Harry Glaser's Website
  7. On Engineering Speed: "Ship early and often. The cost of a small mistake in production is lower than the cost of moving too slowly." — Source: Medium
  8. On Tooling Choices: "Pick boring technology for your infrastructure. Save your innovation tokens for your core product features." — Source: Modelbit Blog
  9. On ML Observability: "If you deploy a model and don't monitor its drift, you are flying blind. Models degrade the moment they interact with real-world data." — Source: Modelbit Blog

Part 8: Philosophy of Technology and Work

  1. On The Tech Ecosystem: "Our relationship to technology is broken. I am done with ecosystems. I am returning to the days when we selected a device, and then an operating system, and then several applications, hacking them together to suit our needs." — Source: Harry Glaser's Blog
  2. On Open Source: "Open source is not a business model; it is a distribution strategy. You still have to figure out how to capture value." — Source: Software Engineering Daily
  3. On The Attention Economy: "The most scarce resource in modern business is not capital; it is the focused attention of your engineering team." — Source: Harry Glaser's Blog
  4. On Hardware Constraints: "We have become sloppy developers because hardware is cheap. Returning to constrained environments often produces better software." — Source: Medium
  5. On Simplicity: "Complexity is a tax you pay on every future feature. Always fight for simplicity in your architecture." — Source: Modelbit Blog
  6. On Mentorship: "A good mentor doesn't give you the answers; they give you a better framework for thinking about your problems." — Source: AppSelekt
  7. On Building for the Long Term: "Optimize for the decade, not the quarter. Decisions made to hit short-term metrics usually harm long-term viability." — Source: Harry Glaser's Blog
  8. On Focus: "Startups don't die of starvation; they die of indigestion. Pick one thing and do it better than anyone else in the world." — Source: Medium
  9. On The Purpose of Technology: "At the end of the day, technology should serve human needs, not dictate them. If a tool makes your life harder, replace it." — Source: Harry Glaser's Blog