Scaling a software business has never been easy. But today—amid macroeconomic uncertainty, depressed tech-stock valuations and even a standoff in Washington (the last time we checked!) over raising the nation’s debt ceiling—it’s more complicated than ever.

So, how can cloud-software leaders stay focused, and continue to grow their companies? Earlier this month, Battery and VC firm FirstMark gathered CEOs from nearly 150 software companies to discuss that topic and brainstorm solutions. At the fifth annual CloudNY conference, held in New York City, speakers from companies representing a combined market cap of more than $50 billion offered concrete advice for others in their shoes, including tips related to leadership, go-to-market strategies and even realizing efficiencies through generative AI.

Here are four main takeaways from the discussion, which included insights from the leaders of companies including Braze*, Datadog*, MongoDB, Vimeo, Airtable, Arize AI*, dbt Labs and Synthesia.

1. Efficient growth in today’s market requires involved leadership–without gumming up the operational works.

Dev Ittycheria, president and CEO of the publicly listed database company MongoDB, warned that senior leaders tend to become detached from daily management as their companies grow. To remain connected to his firm’s operations, he’s instituted a non-negotiable Monday meeting at which he and his executives review the state of the business. This practice keeps leadership in touch while accelerating decision-making, he said. Dev urged leaders to have what he called a “learning mindset” and pay close attention to communication, understanding the biases they have. In Dev’s mind, when leaders think they know everything, they no longer recognize their blind spots or areas of improvement — and that’s where they fail. The best leaders are very aware of themselves, their teams and the situations around them.

2. Leadership takes guts, listening skills and instinct, especially now.

Anjali Sud, CEO of the video marketing platform Vimeo, and Bill Magnuson, co-founder and CEO of Braze*, a customer-engagement company, also shared their hard-won leadership lessons. Bill noted the valuable guidance he had received from his VC backers on what to expect as his company grew and the organization became more developed. Anjali emphasized the importance of staying close to customers and paying attention to their feedback, needs, and wishes. This input, she noted, creates a vital balance to the advice given by her investor team. “It’s easy to forget how important [talking to customers] is,” said Anjali.

3. Cracking the GTM code means preparing for change.

Howie Liu, co-founder and CEO of cloud collaboration service Airtable, and Tristan Handy, founder and CEO of dbt Labs, a database-software company, spoke about how their perspectives on sales and customer relationships changed as their companies grew. Tristan noted that dbt Labs’ eventual pivot to enterprise sales after initially relying on word of mouth was difficult. Growing out of a consulting firm, dbt Labs’ early customers were companies with their own eight to 12 person data team, but dbt Labs realized in selling to the enterprise that many enterprises did not have a data team in the same way as those early customers. This meant relearning for whom they were creating products and redefining their target buyer persona.

The boom of 2020-2021, Tristan said, made it difficult to discern true market feedback, since “we could’ve done anything, and it would’ve worked. It’s hard to get good signal in that environment.” Now dbt Labs has become more disciplined and precise in how it approaches enterprise buyers with the target persona.

Howie related a similar experience at Airtable. The company generated so much initial interest that the team discounted the advice to define a buyer persona and a go-to-market (GTM) plan. Later, the team retroactively discovered the wisdom in that guidance, recognizing that early adopter audiences are fundamentally different from later customers who will pay up for the product. The Airtable team, like dbt Labs, had to change its target customer and its sales approach.

In a later discussion on growth, Olivier Pomel, co-founder and CEO of Datadog* emphasized the importance of linking the sales and product teams. In an unorthodox move, Datadog’s sales team initially reported into the product team. This provided the product team with a clear understanding of who was buying the product and why those customers valued it. To make the product team comfortable talking with customers and to ground it deeply in the pain-point Datadog was solving, that group worked with the sales team in the initial product launches. As Olivier noted, “A good product is better than the best sales.”

4. Generative AI is here to stay. Is your data ready?

Finally, CloudNY also addressed the red-hot topic of generative AI in a discussion with Aparna Dhinakaran, co-founder and chief product officer of the machine learning observability platform Arize AI* and Victor Riparbelli, co-founder and CEO of Synthesia, an AI video-creation company. Aparna and Victor both urged attendees to experiment with generative AI and integrate it into their businesses in as many ways as possible—content creation, customer service, basic coding and such—to keep up with the innovation in the sector. Leaders must also learn how to evaluate the adoption of LLMs, to see generative AI not as hype for hype’s sake but as a high-utility tool within a business.

Synthesia’s Victor notes that data is the critical differentiator with tools like ChatGPT: “Those who have quality data will win, because you’re only as good as your model inputs.” Aparna believes that the key to success is making your AI products easy for customers to adopt. Both Victor and Aparna agreed that operational support is critical for democratizing the power of training LLMs rather than leaving it to the large tech companies.

We’ll be unpacking more insights from this rich panel discussion in a future edition of our “Condensing the Cloud” Substack — subscribe now if you haven’t already!

The future of cloud is bright

While the short-term economic forecast may be hazy, our team believes strongly that cloud software’s longer-term prospects are still bright. With the dramatic changes rolling out across the economy and the tech industry, the cloud sector is sure to evolve in unexpected ways over the next year. CloudNY gave us a chance to pool our experiences and best practices as a community while building lasting relationships across the industry.

We hope to see you at the 2024 CloudNY conference!