Portfolio Interview: Drew D’Agostino | Crystal

The HubSpot Ventures portfolio is full of founders who have valuable knowledge and expertise in successfully building SaaS companies. To tap into their wisdom, we have conducted interviews with these founders and will be sharing their insightful responses in a new LinkedIn Series called "Portfolio Interviews".

First up, Drew D’Agostino, Founder and CEO of Crystal. Crystal is a personality data platform for scaling behavioral intelligence and excellent communication skills across the entire organization, from junior team members to senior executives.

What were the biggest challenges you faced when launching your SaaS startup?

We had a brand new technology in 2015 without a real software category. There was just such a large degree of ambiguity, so it took a while to figure out how to sell effectively and deliver recurring business value.

Who or what has had the most influential impact on your company?

There are several books, advisors, and mentors I can point to at various stages of the company.

Some of the most impactful books were How to Win Friends & Influence People, Influence, Zero to One, and Principles. I’ve also been reading bloggers like Jason Lemkin and Seth Godin for years, so I’m sure their content has shaped my thinking.

I’ve also taken the most inspiration from products like G2 , Slack, and especially HubSpot. To be honest, no company has influenced Crystal more than HubSpot, both in the product and business sense. Several current and former HubSpot executives personally supported us for years, like Christopher O’Donnell, Brad Coffey, and Dharmesh, among others.

Are there any specific features or functionalities of your product that align well with the needs or workflows of HubSpot users?

Yes, two specifically:

1. Direct HubSpot CRM enrichment with Crystal personality data.
2. Pre-meeting reports for target accounts and key executive contacts.

Have you received any feedback or testimonials from HubSpot customers that highlight the benefits or positive impact of using your product in conjunction with HubSpot?

Yes. One example is from a HubSpot partner Babelquest. They use Crystal data extensively with their clients, in multiple stages of the GTM process.

Can you share any upcoming features or updates to your product that may be of interest to HubSpot customers?

Yes, we are launching a new pre-meeting intelligence service for companies who need deep, enterprise-level insights about key executives. This service combines our proprietary datasets and technology with highly efficient, AI-enabled human research, so any GTM team can have access to the same quality research that we typically only see at Fortune 100 organizations. 

What are your thoughts on bootstrapping versus seeking funding for a SaaS startup?

My thoughts have evolved significantly over the years.

I now believe companies should view equity funding more like debt. It’s sometimes necessary, but if you raise too much, it has the same impact psychologically as borrowing too much. This can create a bias towards short-term thinking, rather than long-term sustainability. It may also insulate you from reality — when you have a cash cushion, it’s easier to tolerate mediocre results. Bootstrappers don’t have the luxury of mediocrity, whether it’s in the product, team, revenue, or strategy. 

However, I’m also a big believer in raising early from angels and strategics who do not have a specific time horizon. They can be incredible partners, especially when they have real skin in the game. Crystal’s angel investors have become some of my strongest professional connections, and few have become close friends as a direct result of our many conversations about the business. 

How did you build a team around your SaaS startup? Any tips for finding and attracting top talent?

I’ve hired lots of people over the past 9 years with Crystal, made mistakes, and finally learned some really valuable lessons. A few of those lessons: 

• Fill the team with mostly up-and-comers, but absolutely make sure you have a couple of very experienced leaders (I’ve swung too far in both directions before).
• Think in terms of 4-year tours of duty, where both the company and employee are clear about the outcome they want, and they mutually try to help each other achieve it. It’s a culture of transparency that I got from the book The Alliance by Reid Hoffman.
• Prioritize “group” hiring when possible (bringing in folks who have worked together). People who have experience working together have a high floor, and they stick around when it gets tough.

What advice do you have for founders exploring taking strategic/corporate VC money?

Actively seek out assistance, rather than waiting for it to come. Corporate VCs have a lot of resources, so you can leverage their network, knowledge, and size.

What is your unique value proposition? Are you in a crowded market or a market that requires customer education?

More on the educational side. We are shifting and focusing our value proposition for GTM teams to “be the most prepared person in the room,” using our data to accomplish that goal.

How do you see AI influencing the competitive landscape of the SaaS industry, and how are you staying ahead of the curve?

It’s getting noisier and harder to understand by the day, but here are my current thoughts: 

• We’re getting close to the peak of the hype cycle, and we’re likely to enter into a “trough of disappointment” soon. Many people have allowed their imaginations to run wild, setting impossible expectations for AI tools in their current state. 
• That said, I think AI is finding some serious product-market fit in several “behind the scenes” functions, and that is starting to compound in ways that are invisible to most users.
• The chat interface of AI seems to be a temporary bridge – the most effective use cases I have seen for AI are baked into the product, where the user has no idea they’re using AI; they’re just getting better results, faster.

Right now, AI is impacting our business by helping us generate content and insights more efficiently. It’s a major component of the new intelligence services we’re launching this year. We’re also focused on building and optimizing our proprietary datasets, so our predictive models always have a unique advantage over generic LLMs for their specific aims (i.e. predicting personality traits).

In your opinion, what are the biggest opportunities that AI presents for SaaS businesses and their customers?

Who knows how these technologies evolve in the coming years, but in this early stage, I think AI is immediately useful for scaling and optimizing back end processes where 80% accuracy is “enough.” I still don’t think AI is ready to replace many software tools for non-technical end users, and like I mentioned before, I think the chat interface is a temporary novelty. But under the hood of a SaaS product and a SaaS GTM process, there are many micro-processes that can completely be redesigned and rebuilt more effectively with an AI-focused approach. It’s a no-brainer decision to give your team access and play with it, to see where the best use cases organically emerge.

What does being customer-first mean to you and your team, and how does it guide your decision-making and strategic planning?

Two things come to mind:

1. Executives should always have active, personal relationships with customers and involve them in key company decisions.
2. The company should have a really strong feel for the “pulse” of the user base. Everyone should be able to answer simple questions like “who are our most active users?” “What are the most important actions in our product”

Can you share a specific story or example of how a customer's input or feedback led to a significant change or improvement in your product?

Yes, we’re building a whole new product based on the usage of our enterprise customers. They revealed a very big opportunity.

Can you share any specific initiatives or practices that have helped foster a customer-centric culture within your organization?

Using our customers and users real names, roles, problems, etc rather than speaking in abstract terms. This actually has a really big impact!

Learn more about Crystal: www.crystalknows.com

Learn more about HubSpot Ventures and our portfolio: www.hubspot.com/ventures