After 10+ years as a CEO of Gainsight, considered to be the father of the CS function and now running a several hundred million USD ARR business, he’s certainly learned a few things on this amazing journey, and in an exclusive workshop for the SaaSiest CEOs, he went into the details about this. Today we have the pleasure of bringing you a condensed version of those learnings:
- Keep High Standards for Leadership
Leadership shall at all times be required to maintain the highest standards. Apply a process to enable quick, decisive action when leaders don’t align with your values. This approach ensures the team’s success and respects your core principle of treating others as you’d like to be treated. - Trust in the Initial Team
The initial, often scrappy team of a startup is critical for success. While the temptation to “upgrade” the team exists, the experience at Gainsight taught us the value of internal promotions and believing in those who have been committed to the company’s vision from the start. - Scale with Caution
Scaling decisions should be based on clear leading indicators, not assumptions or overly aggressive forecasts, especially in times like these. Past scaling missteps have underscored the importance of prudent, experiment-driven growth strategies. - Early Standardization of Pricing
The complexity of custom deals and varied contracts can become unmanageable. It is tempting to have special pricing, particularly for that special logo you so wanted, or the new enterprise segment you are breaking into to. But refrain from doing it to the extent possible, as it becomes difficult to maintain in the long term! Early investment in standardization and back-office systems is essential for scalable and clear business operations. - Embrace Digital Customer Success Early
A high-touch, customer success model is not easily scalable. Investing early in digital engagement tools and self-service options is key for sustainable growth and customer retention. - Human-First Departures
All relationships—be they with employees or clients—should end positively and with gratitude. This approach aligns with our ethos of valuing human connections and fosters a culture of respect and learning. A perfect example here is when you have colleagues that leave you. Don’t be mad, and don’t be disappointed, instead find a way to congratulate them on their next step, thank them for their dedication to you in the past, and welcome them back whenever the time is right. Be nice, be human! - Prescriptive Methodology
Establishing clear, expert-driven methodologies early on is crucial for guiding clients effectively. This approach simplifies onboarding, improves value delivery, and supports continuous product engagement. Having a process for all key functions is super important from day. - Proactively Seeking Growth Opportunities
Plan for phase 2/3/4 way before you think you need to! Anticipating market saturation and exploring new product avenues early are vital for sustained growth. Delaying the development of a “second act” can stunt a company’s momentum and attractiveness to investors. - Patience Over FOMO
Staying true to core values often leads to better long-term success than yielding to the fear of missing out (FOMO) and making hasty decisions based on external pressures. We’ve all been here, and seldom pays off to jump on the next big thing just because it is trendy. - Authenticity in Leadership
The power of authenticity and vulnerability in leadership cannot be overstated. Embracing and sharing one’s true self fosters deeper connections and trust within the company and beyond. Nick shared a fantastic example where early on in his career he had been advised by a PR firm to dress a certain way, speak a certain way, and basically create a persona that they thought would fit the market…the outcome…when you are not true to yourself you won’t be the best version of you. You do you, be real, be authentic, it is the only way to build meaningful relationships with customers, colleagues, partners, and investors.
