Stay SaaSy is about scaling, managing, and leading growth stage startup teams, with a particular emphasis on product and engineering.
We believe that advice should be actionable, regardless of whether the topic is lofty and strategic or low-level and tactical. To help you find posts that are most relevant to your situation, we’ve broken our posts into categories below. If you want to know where to start, scan through the headings to dive into areas where you have specific needs.
Thanks for reading!
For Executives
For Executives of All Sorts
Much of our experience comes from executive-level leadership: Building and running departments in high-scale environments. Here is advice for executives and leaders of all types.
- Don’t Create Chaos
- Don’t Bring Me Problems, Bring Me Solutions
- Fair But Unequal
- A Practical Guide to Executive Presence
- How To Run a Department
- How To Be a Senior Leader
- Working Across Departments
- Avoiding The One Step Back
- Proactive vs. Reactive Teams
- Management Scrutiny
- Consistent Caliber Teams
For Heads of Product
- Your Head of Product and Your CEO
- When To Hire Your First PM
- Finding and Fostering Great Product Sense
- How To Be a PM That Engineers Don’t Hate
- Battlefield Product Management
- Don’t Build Useless Features
- The Swiss Army Product Management Team
For Heads of Engineering
- How To Be an Engineer That PMs Don’t Hate
- Competitive Analysis for Engineers
- The Most Important Performance Management Rule for Software Engineers
- Stop Writing Great Runbooks
- Managing Engineering Managers: A Primer
- Picking Your Tech Stack for Dummies (and the Future)
Team Structuring
For Managers of All Sorts
General Management Advice
- Soft Skills for Managers
- Advice to New Managers: Don’t Joke About Firing People
- (People On) Nice Teams Finish Last
- Stop Making People Make Up Their Mind
- On Achieving Goals
- Traits You Can Change, and Traits You Can’t
- Small Performance Cues
- Managers Should Optimize Job Satisfaction, Not Happiness
- Goals, Problems, Solutions
- Simple Ways To Be Less Divisive
- Check Up On Your Team’s Kids
- Have Bad Days and Let Others Have Them Too
- How Satisfied Are You With Your Job, On a Scale of 1-10?
- Three Types of Management Problems
- Unforced Errors
- Optimize Onboarding
- Transparency Is The Key To Accountability
- Manager Superpower Series: Optimism
- Stop Blocking Things At The Last Minute
- Promote Imperfect People
- Advice to New Managers: Don’t Joke About Firing People
- Writing Performance Reviews 101
- Creating Good Process
- The Three Minute Guide to One-on-Ones
Recruiting
- The SaaSy Guide to Hiring
- Value Sell Recruiting
- The Intangible Skills You Can’t Interview For
- How I Read Product Manager Resumes
- The Most Valuable Question When Interviewing Managers
- Maximizing The Value of Reference Calls
Meetings
- Give People Something To Look At
- Everything I’ve Learned About Running Meetings Comes From Not Wanting to Be There
Product Strategy
Selling to the Enterprise
Here’s our post series on how to build a highly sellable enterprise B2B product.
- Selling to the Enterprise
- Challenging SaaS Incumbents
- Be Enterprise Ready
- Crafting Product Narratives
- Which Competitors Matter?
- Expand the Playing Field
- Avoid Saying No
SaaS Strategy
- Enterprise Retention Means Solving Hard Problems
- How To Improve Your Gross Margins
- Ways To Expand Your SaaS Business
- Unlimited Is a Ponzi Scheme
- Product Roadmap Detours
Using Data
Startup Scaling
Much of our experience comes from building teams and improving processes in very high growth environments. Here’s a compilation of topics related to rapid scaling:
- The Hardest Part of Working at a Growth Startup
- Optimize Onboarding
- Startup Make-Believe
- Thoughts on Product-Market Fit
- Starting Software Teams: Avoiding Big Mistakes
- Rooting Out Red Tape At Your Startup
- Culture Viruses
- Management Debt
- Low Context – Software’s Silent Killer
- Complexity Debt
- Where To Innovate, Where To Imitate
- Low Priority Issues + Time = Relationship Killer
- 7 Reasons Your Growth Startup Is Hiring Too Junior
- The Rogue Wave of Enterprise SaaS
- The Hardest Part of Working at a Growth Startup
- The Perils of Startup Engineering
- I’m Building a Startup – Is This Normal?
Careers and Onboarding
- New Hires: Learn How The System Breaks
- Moving from IC to Engineering Manager
- Negativity Bias, I Love You But You’re Bringing Me Down
- Build Your Career On Dirty Work
- Good Managers Write Good
- Working With Integrity
- Debugging My Work Health
- Stop Looking For Mentors
- Things 10x People Do
- Reframing Imposter Syndrome
- Soft Skills for Managers
- Grow Skills With Work, Not Extracurriculars
- Stop Sabotaging Your Career With Short Stints
- My Superpower: Waking Up Early
Situational Guides
Special Situations
Here are some of our situation-specific guides, for team members of all levels who are handling rare but critical situations.
- DEI for Dummies
- The Future of Remote Work
- Compensation Heuristics
- How Acquirers See Your Company
- How To Give Bad News
- What to Do When Your Team Quits
References
We’ve put together several reference lists for various startup phases.