20 Questions Every CEO Should Ask While Building a SaaS Company

Bootstrapped founders know all too well that the journey from “idea” to $10M… $50M… and eventually $100M of ARR is overwhelming. There are countless things to consider as you grow your organization, spanning from product to economic modeling to company culture.

At our 2024 CEO Summit, Mainsail’s Vinay Kashyap presented a compelling framework to help CEOs find structure in the way they think about company growth. He proposed:

What 20 questions should every CEO ask while building a SaaS company?

Of course, there are more than 20. But the objective was to help CEOs narrow their focus to some of the technology, culture and sales considerations that we believe are impactful to accelerating growth.

The full list is below, with helpful anecdotes from our CEO Summit and prior posts from Mainsail. For founders who are still bootstrapped, you will notice examples of how working with an investment partner that is experienced in these operational areas can better equip you to tackle these important questions head-on.

DO YOU HAVE A COMPELLING AND SUSTAINABLE VALUE PROPOSITION?

1. How often is your product used — daily? weekly?

2. How many people and different roles within your customers’ organizations use your product and where do you fall in their software priority stack?

3. What is the ROI of your product? Think about how often and accurately you measure the ROI of your product. Do you sell with ROI in mind? Can you offer an ROI calculator as part of the sales process?

4. How much pain would your customer feel if your solution went away?

Deep Dive: If the answer is “not enough to retain them,” how can you flip the script? At our CEO Summit, one Mainsail portfolio company shared a case study on how it combatted attrition by focusing on sticky customers and adjusting its value proposition using these four strategies:

Identify the root cause of the churn and better align your product roadmap and pricing to provide customer value
Sell exclusively to your ICP and have the guts to say “no” to those that don’t fit your ICP
Align onboarding to the full customer journey to drive adoption from the start
Operationalize the payments portion of your offering

The company doubled down by aligning organizational goals and structure to these initiatives, going as far as to use monthly board reports to hold the full team accountable. As a result, they increased both NRR and logo retention and achieved more efficient ARR growth.

5. What software are you sitting next to, and can you buy or build it?

Deep Dive: Another Mainsail CEO shared that, while his company had a strong value prop, a well-defined ICP, and a solid GTM motion, they had an opportunity to move up-market by acquiring an adjacent brand. They believed that by re-platforming and re-negotiating their payments process, they could launch a new pricing model that would drive revenue and efficiencies.
Identifying and leaning into their own strengths, the company leveraged M&A to create a product with a stronger overall value proposition.

ARE YOU BUILDING DURABLE COMPETITIVE MOATS?

6. What is your market share today versus the competition?

7. Do you have measurable brand recognition, trust and thought leadership in your industry?

8. Do you have durable product superiority, stemming from real market insights?

9. Are you using data in your product and marketing that your competitors can’t use or don’t have?

Deep Dive: At the CEO Summit, another portfolio company shared how it leveraged AI to enrich its dataset around a key ICP. They had been lacking in historical data for this ICP and needed to identify the highest ACV accounts to pursue. The resulting data increased the company’s target list by 3X and allowed them to refine their positioning and messaging for this key customer segment. By using data to fortify their ICP definition and outreach, the company was able to position itself ahead of the competition.

HOW ARE YOU STRENGTHENING YOUR ECONOMIC MODEL?

10. Are you using AI in your operations to drive efficiency?

11. How quickly is your ARR per customer increasing?

12. How quickly are you improving your sales and implementation cycle time?

13. Do you have predicable and improving customer and revenue cohorts that support your CAC? Are you analyzing these with and without various products?

Double Click: Mainsail’s VP of Customer Experience, Jess Bicknell, provided a roadmap for effective cohort analysis in her post, “Why and How a CX Leader Should Implement a Customer Segmentation Strategy.” Check out her suggestions for defining customer segments across various dimensions, conducting cohort analysis and acting on the insights derived from these segmentation exercises.

14. Are you capturing a fair share of economic value through thoughtful and optimized pricing and packaging?

Double Click: Mainsail’s 2022 Bootstrapped Sentiment Survey revealed that more than half of bootstrapped founders were planning to change their pricing in 2023. Yet, according to Mainsail’s VP of Pricing, Brian Russell, the mistake that many companies make is solely focusing on whether they should increase or decrease current prices.

In his post, Evaluating Your Pricing Model, Russell emphasizes that, “You cannot set the right price with the wrong price model” and offers ideas on how to approach pricing metrics and packaging in a way that can help optimize product value.

IS YOUR CULTURE CUSTOMER-FOCUSED, DATA-DRIVEN AND PERFORMANCE-ORIENTED?

15. How do you stay close to the Voice of the Customer?

Listen In: “Make your customers heroes” was one of Kyle Lacy’s Six Lessons Learned Scaling High-Growth Software shared in a recent webinar with Mainsail’s VP of Marketing, Matt Buckley.

Lacy suggested how growing SaaS businesses can stay close to the Voice of the Customer:

Create a customer advisory board early in your maturity
Feature case studies prominently on your website and marketing materials
Invite customers to present on webinars and at conferences.

After all, says Lacy, “Your customers are your best champions.”

16. How often do you get in front of your customer in the field or as a group?

Double Click: Not sure when to start? Jason Lemkin of SaaStr recommends hosting your first customer event when you hit your 100-customer mark. Mainsail’s Senior Director of Demand Generation, Mike McEuen, wrote in The 7 Steps to Nail Your Customer Event, “pulling off a great customer event involves putting a plan in place, thinking about the customer experience with every detail, and working together as a team.”

17. Do you have a culture of joy, a mission-driven orientation, and diversity of thought?

Double Click: For companies that are growing quickly, a strong company culture is paramount to retaining good talent and creating happy and effective teams. In 2023, Mainsail hosted a webinar with our partner Breakline Education called, “Don’t Give Up on DEI – Why it Still Matters and How to Enact It Effectively.” Breakline’s CEO Bethany Coates provided actionable ideas for nourishing diversity of individuals and ideas within your organization, so you can create a genuinely robust culture.

18. Do you have a culture of experimentation and innovation? How many concurrent experiments are you running in your business right now?

19. Do you have a culture of accountability?

If you’re paying attention, that’s only 19 questions. So, the 20th is up to you: What do YOU think is the most important questions to ask yourself and your team as you strive to become a leading SaaS business in your space? Comment here on our LinkedIn post and we’ll report back on the answers here and on our LinkedIn post.

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