Community Spotlight: Conor Dragomanovich

Product-Led Sales (PLS) Community Spotlights were born out of a desire to celebrate members of our PLS community. In this series, we shine a light on our forward thinkers, uncovering the career paths that brought them to the product-led space and highlighting their advice and predictions about the future of PLS. 

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Meet Conor: Director of Commercial Sales at Productboard

Conor Dragomanovich has a knack for joining companies right before they explode.

Conor was the first account executive (AE) at Productboard, a customer-centric product management platform, back when the company was about 30 people and before they raised their series A. Today, he’s the Director of Commercial Sales at the series D unicorn (most recently valued at $1.7B). 

Before that, Conor was the founding AE at DealPath, where he helped lead the development of their go-to-market (GTM) motion, playbook, and ideal customer profiles (ICPs). His career in tech sales started with an SDR role at AppFolio, where he grew to become an AE before moving on.

Given this track record, it’s no surprise that Conor describes a “fascination” with startups. 

Conor: “Right from the get go, I had developed this fascination with early-stage companies and what the journey looks like from pre-seed all the way to IPO. And I knew that when I transitioned from AppFolio to my next role, that it was going to be a very early stage company.” 

What made Conor switch from Education to Sales? 

Growing up in a family of educators, Conor was on track to become a university professor when a job listing lured him into the sales world.

But, as it turns out, selling had always been in his bones. 

Conor: “In reality, I guess I was always in sales. I was a very entrepreneurial young person. I would sell photographs of the kids on my baseball team to their parents. If it wasn’t that, it was Pokémon cards and baseball cards.

“And then, while I was going to UCSB, I actually managed surf shops up the coast of California. I was an area manager where I would go from store to store and inspect the stores and help them sell GoPros, surfboards, skateboards, all that good stuff. So when it came time to either put up or shut up in that professorial track, I started wondering if it was still for me. I decided to take a break.”

While taking that time off, Conor stumbled upon the AppFolio SDR job listing. The words “B2B,” “SaaS,” and “SDR” had little significance to him at the time, but he went for it anyway. The rest is history.

“We were seeing thousands and thousands of inbound leads that felt, at the time, like gold in the rivers that was there for us to scoop up. But of course, there's more to that story.”

The Progression From Founding AE to Director of Commercial Sales

Of course, Conor’s role has seen quite the evolution as he’s gone from an AE to a director in just over 3.5 years at Productboard. The path looks something like: creating early sales processes to build on a successful PLG motion >  identifying market approach and ICPs > fleshing out the team >  defining the outbound technique > developing a new enterprise sales motion.

Let’s explore that path in a little more detail. 

When he began as the founding AE, the first order of business was defining the sales process and identifying where it could further the success they already had with their product-led growth (PLG) motion. 

Conor: “There wasn't a defined segment at Productboard at the time. There weren't really defined sales roles either. I was just an account executive who was trying to figure out how we were going to sell it, because Productboard is such an intuitive and sophisticated product. They'd had so much success from that PLG motion. They'd already managed to see some really exciting and compelling growth just from the customers who were coming in, experiencing the product for themselves, swiping a credit card, and signing up.” 

At the time, Conor says an influx of thousands of inbound leads felt like “gold in the rivers” for someone like him who was accustomed to outbound. So a major part of his role was finding the right approach to the market and using data to narrow down leads with product fit. 

Conor: “We started to parse the data that we got from trial signups to identify the low-hanging fruit. We started to identify which trial signups actually fit into the category, the persona, the business profile that we wanted to actively prospect and try to convert.”

At the same time that they were developing the sales process, they were also working to build out playbooks, ICPs, and, of course, a team. 

Conor: “As I and other early sales hires joined the company, we were tasked with understanding what that selling motion would look like. We took part in the development of sales playbooks and really configuring and understanding who our ideal customer profile was. 

“In addition, that first year was very much focused on building out the team — hiring our first SDRs, other AEs, starting to carve out some rough segments around where we wanted to penetrate the market in terms of SMB and mid-market, and so on.” 

With a team in place, their focus eventually shifted to creating a new outbound approach. From that, an enterprise sales motion was born. 

Conor: “A lot of the early days was just making sense of the inbound volume that we were getting. And then doing research and documentation around what an outbound motion would look like based on those learnings. 

“From there, it transitioned into figuring out if we could be successful selling enterprise deals. So I slotted into an enterprise account executive role and did that for a year to a year and a half, where I helped land some of our largest partnerships at that time.

“We had seen success down-market within the SMB space and through the self-service motion, so we wanted to see if we could replicate that success up-market. We proved we could through partnerships with companies like Here Technologies, Zendesk, UiPath, Zoom and more.” 

How Conor Initially Defined ICPs

In the early days of fleshing out the sales motion, Conor and his team relied on a mixture of insight, common sense, and data to inform their initial ICPs. Where did they get this information? Primarily, it came from:

• Input from their customer success team
• Data enrichment platforms 
• Productboard’s own usage data
• A realistic look at the volume their sales organization could support at the time

Conor: “We leaned a little bit on the very small customer success team we had and the limited tech stack that was available, tools like Salesforce, Clearbit, MadKudu, Looker, and so on. And of course we looked at the backend of Productboard, which provides an administrative console to understand some usage data. 

“We took this information and we drilled deeper to find answers to questions like: What are the right verticals for us? What is the right customer profile? What is the right segment? Where are we seeing the most interest from? That helped us develop a rough profile based on the size and type of a customer, in terms of product manager, group product manager, product director, VP of product, or CPO.

“Finally we thought about the size of the business, because we knew we weren’t prepared to support 5,000+ employee companies that had complex product organizations. We knew that we needed to start within that zero to 2,500 space.”

Conor’s Outlook on the Early-Stage AE Profile 

A skill that all AEs should have, according to Conor, is the ability to leave their ego at the door — but not their enthusiasm for the job. 

Conor: “You want to have a very low ego, or no ego to the extent that it's possible. You can go in with a lot of enthusiasm and pride in being the steward of the sales team, but you're going to have to wear a lot of different hats and that’s going to be a very humbling experience with regards to all of the things that you don't know.”

But for AEs entering into growing companies specifically, there’s another special trait they should have: empathy. In early-stage organizations, it’s crucial that sales should be able to see beyond their silo and understand the POV of their counterparts across product, engineering, marketing, and customer success.

Conor: “I think having high emotional intelligence and a lot of empathy for what your cross-functional partners are going through is really important. If you come from an organization where you’ve been siloed in the sales organization, that's often all you see and think about. But as an early-stage account executive, you work so closely with your counterparts in product and engineering and marketing and customer success that you need to develop a really keen sense of empathy for what it is that they're experiencing and what their challenges are.

“One of your jobs will be identifying and reducing friction points in these relationships so that you can work much more cohesively as an early-stage team. This wouldn’t necessarily be a part of the profile for a new AE at a 500-person company.”

“I think having high emotional intelligence and a lot of empathy for what your cross-functional partners are going through is really important.” 

The Best and Worst Parts of Your Job Today

As an AE, the element of the job that Conor enjoyed the most was, no doubt, working with product folks. 

Conor: I've sold to a lot of different personas and profiles, and working with product managers and product leaders has been such a refreshing experience. They are every salesperson's dream. They're deeply thoughtful. They're extremely curious. They're not shy with communication. They're extraordinarily forthcoming about what it is that they're trying to accomplish and have a healthy understanding of what sort of risks and challenges are involved in that.” 

Now in a leadership role, Conor enjoys the opportunity to help his employees flourish. 

Conor: “The best part of my job now is being able to identify, develop, and help the members of my team move forward in their careers. That by far is the most fun and the most rewarding part of the job.” 

Of course, it can’t be all upsides, all the time. Conor’s biggest challenge today is recognizing how Productboard is different now than it was in the early stages, and that “go go go” isn’t a necessary mentality anymore. 

Conor: “I always want to go faster and faster. The hardest thing for me is reminding myself that it's OK to be in the position we’re in. It’s not always about exponential expansion. The growth that we saw from A to B might not be the growth we see now. The struggle that I have is reminding myself that there are very new challenges and goals in every stage, and that’s a good thing.”

What Advice Would You Give Someone on the Same Career Path? 

Conor has two pieces of advice for others who are early in their sales career, one more tactical and one more philosophical:

• Document everything 
• Don’t just accept that you'll fail sometimes — lean into it

Conor: “The first piece of tactical advice would be to document everything. The second piece of advice would be: be less afraid to fail.

“I think you really do have to lean into failing, and failing fast. Early on at Productboard I felt like I shouldered so much of the responsibility for the success of the company as a founding AE that my risk threshold was lower than I think it would've been and maybe should’ve been otherwise.” 

The Future of Product-Led Sales, as Told by Conor

When asking Conor what he believes the future holds for Product-Led Sales, it was interesting to hear that his answer aligns with what many other pros we’ve talked to have said: it’s going to be all about finding a balanced hybrid approach. 

Conor: “Right now the concept of being product-led is spoken about like it’s a binary — you're either product led or you're not. But my expectation is that businesses will do both.

“There will still be the top-down sales motion where you need strategic enterprise AEs working with executive leaders on a top-down initiative to roll out a system for the business. But that doesn't preclude the business from having a PLS motion as well.

“What I see coming is greater facilitation and understanding of how to have hybridity with a PLS motion as well as a more traditional enterprise sale motion. I think they can work really well together, and PLS can still inform the work that an enterprise AE is doing.” 

Rapid-Fire Questions: Faves Edition 

Favorite TV show? The Marvelous Mrs. Maisel 🎙️

Favorite emoji? 🤯 

Current travel fantasy? 🇩🇪 Berlin. That’s where I was already planning to travel, just weeks before COVID hit. 

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