Dear SaaStr: When a Customer Says “That’s Too Expensive”, What Do You Do Next?
Dear SaaStr: When a Customer Says “That’s Too Expensive”, What Do You Do Next? When a customer says, “That’s too expensive,” it’s not necessarily a deal-breaker—it’s often just an opening to a deeper conversation. Or more often a...
What To Look For In Your First Marketing Hire
Dear SaaStr: What Do I Look For In My First Marketing Hire? Hiring your first marketing leader is a pivotal moment, and it’s easy to get it wrong if you don’t approach it strategically. The vast, vast majority of “marketers” are just not the right fit to...
Dear SaaStr: What Are The Top 10 Metrics to Track Sales Velocity and Adoption of Our SaaS?
Dear SaaStr: What Are The Top 10 Metrics to Track Sales Velocity and Adoption of Our SaaS? To measure sales velocity and adoption rate effectively, you need to focus on KPIs that give you insight into how quickly deals are moving through your pipeline and how well...
10 “Simple” Ways to Increase Your Win Rates
Dear SaaStr: What Can I Do To Increase My Win Rates? Increasing win rates in sales is all about focus, discipline, and alignment across your team. Here’s how I’d approach it: Identify Your Top 3 Feature Gaps — And Just Start Closing Them: Start by figuring out...
Dear SaaStr: How Much of My ARR Can I Spend on Customer Success?
Dear SaaStr: How Much of My ARR Can I Spend on Customer Success?’ You can target spending 5-10% of your ARR on Customer Success and Support combined, depending on your stage and growth priorities. Here’s how to think about it: 1. Early Stage (Pre-Scale, <$10M...
Dear SaaStr: My CRO Candidate Is Insisting on Anti-Dilution Protection. What Should I Do?
Dear SaaStr: My CRO Candidate Is Insisting on Anti-Dilution Protection. What Should I Do? A number of online communities have taught CROs to ask for everything: The most equity The most cash Years to exercise their equity Large payments if they are let go, even for...
Dear SaaStr: How Do I Find Product Market Fit In the Early Days?
Dear SaaStr: How Do I Find Product Market Fit In the Early Days? Find a little bit of it first ;). Just a little bit. And then relentless build on top of that. Finding product-market fit is the single most important milestone for any startup. Without it, nothing else...
Dear SaaStr: Can You Ever Get Past 100% NRR If You Sell Just to SMBs?
Dear SaaStr: Can You Ever Get Past 100% NRR If You Sell Just to SMBs? Yes … but probably not if you are single product, and don’t go at all more upmarket. SMBs churn at the highest rate, often as high as 3% a month for the lowest end of SMB / prosumer. So...
Dear SaaStr: Should I Remove Monthly Subscriptions to Drive Down Churn?
Dear SaaStr: Should I Remove Monthly Subscriptions to Drive Down Churn? Generally — no. Annual plans only mask churn. They don’t eliminate it. And at least for SMBs and prosumer customers, not having a monthly edition can add significant friction to...
Dear SaaStr: We’re at $13m ARR and Growing — But Our GRR is Slipping. What Should We Do?
Dear SaaStr: We’re at $13m ARR and Still Growing — But Our GRR is Slipping, Down to 88%. What Should We Do? First off, congrats on hitting $13M ARR and 1,000 clients—that’s no small feat. But yeah, 88% GRR is a red flag, especially at your scale. If your...
Dear SaaStr: How Do I Get Customers to Switch From a Competitor When There’s a Significant Migration Process?
Dear SaaStr: How Do I Get Customers to Switch From a Competitor When There’s a Significant Migration Process? Yeah, that’s the killer. Migration is the Achilles’ heel in stealing customers from an incumbent. Too many founders don’t fully get it. And 95%+ of sales...
Dear SaaStr: What Will Need to Change The Most As We Approach $100m ARR?
Dear SaaStr: What Will Need to Change The Most As We Approach $100m ARR? At $100M ARR, everything changes. It’s a whole new game. The challenges you face at $50M ARR will feel like a warm-up compared to what’s ahead. Here’s what you can expect as you scale to $100M:...
Dear SaaStr: How Do I Monetize a Product Without a Clear Budget Line Associated With It?
Dear SaaStr: How Do I Monetize a Product Without a Clear Budget Line Associated With It? First, bear in mind every organization from the smallest SMB to the largest enterprises has some discretionary budget. When I was a VP at F500 Tech Company, I was the most junior...
Dear SaaStr: What Are The Top 10 Things To Put in a Series A Deck?
Dear SaaStr: What Are The Top 10 Things To Put in a Series A Deck? The most important components of a Series A pitch deck are: The One-Slide Summary. Make The First Slide Sell The Deal: Your first slide should sell the entire company on its own. It needs to answer...
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