Starting and Scaling a Sales Team

By Kyra Durko on August 17, 2021

A conversation with Kevin Romani, Head of Global Sales at NS1

A Head of Sales is one of the most important hires a startup founder makes. I recently had the chance to sit down with Kevin Romani, Head of Global Sales at one of our portfolio companies, NS1. Kevin was the first non-founder hire at NS1, over seven years ago now. He was hired to run and build their sales organization. 

In the conversation below, Kevin shares his thoughts on mastering sales hiring, compensation, building culture, and adopting your first pieces of sales enablement software. For founders that do not come from a sales background, this serves as a basic overview of what to expect and start thinking about. 

What attributes are most important to look for in early sales hires? What tactical advice around hiring and interviewing would you give to early stage companies? 

A lot of early stage founders ask me this, and I always give the same answer – it really depends. The biggest factor boils down to the strengths and weaknesses of the founding team. If the founding CEO enjoys being in front of customers and is a naturally good sales person, then you can hire somebody more junior with a lot of growth potential. Someone with just a few years of experience that can still excel at generating leads, managing the sales process, and building out the first version of your CRM. If the founders are more technical in nature and less comfortable in a selling role, you may want to hire someone more senior as your first sales hire. Ideally this person either built a sales team from the ground up before or otherwise has a history of success operating in a startup environment and really knows the space that you’re trying to sell into well. Come up with a profile of what you think you need or want in a first sales hire before you start the process to avoid wasting time.

A salesperson’s job at its core is to be an effective communicator. Instead of creating a few key questions to evaluate a candidate’s attributes, we ask them to go into very deep detail about their experiences. We ask lots of questions about how and why they did certain things. This helps us understand how someone operates and thinks, what motivates them, and how effectively they can communicate these obscure concepts. Get references early on, and do lots of backchanneling. 

Do you have a preference between pulling from another startup versus a large corporation? 

It’s been my experience that people who’ve been in large corporate organizations for a number of years or the vast majority of their career are a little bit less hands on than you might need from early hires in a startup environment. On the flip side, startup people aren’t always the people who can take you from zero to $100 million in revenue. Regardless, you want someone who will be able to roll up their sleeves and execute from day one.

What practices do you recommend implementing from the start to build a strong culture within a sales team specifically?

It’s really important to make sure that you’re clear in terms of what your values are and what kind of company you’re building. I don’t have any magic way to make sure that your values align with the values of the person that you’re going to hire to run your sales org, but if those values aren’t in sync, it can be a pretty stressful situation. You want to make sure early on that everybody’s rowing in the same direction. It doesn’t mean everybody has to be the same or have the same background – diversity of experiences is key – but you do want to make sure that your values are equal and expectations are clearly laid out.

What should early sales hires’ compensation look like? How should it be structured across different compensation types (ie. salary vs bonus)?

First and foremost, you want to make sure your incentive plan is aligned with the goals of the company. The vast majority of sales people will be “coin operated.” Sales reps should always want and need to sell things in order to make their full on target earnings. The most common structure for a sales rep would be 50/50 – half in base and the other half in commissions. Most sales people expect this. 

That said, depending on where you are in reaching product market fit, or what your medium term growth plans are, the earliest sales hire may need to put a lot more effort into building out the initial sales organization infrastructure. For example, they will need to get sales ops hires and software in place, figure out deployment strategies and potentially hire solutions engineers, and develop playbooks. In these cases, you may see comp plans where 50% of the variable commissions is tied to infrastructure deliverables and 50% is traditional sales commissions for hitting bookings goals.

Keep in mind, you should do your best to set your early sales hires up for success. If your product is not ready to go to market, do not expect sales to be easy. If you have no software in place, make sure they have a budget to work with. It will be worth it for everyone.

Let’s talk about tooling. What software should companies consider integrating to be efficient and successful? Is there a framework to group these tools into specific buckets?

I think about sales ops as a three legged stool – revenue operations, sales productivity, and training/enablement. Revenue operations encompasses collection and analysis around your sales data (sales cycle, waterfall metrics, pipeline creation, pipeline coverage needs to hit goals, etc). Software that falls into this bucket would include BI tools like Microsoft BI, Tableau and CRM platforms like Salesforce. Within the second leg of the stool, sales productivity, are communication tools like Outreach and LinkedIn Navigator, note taking tools like Dooley, Quip, Otter and Notion. Within the third leg, training and Enablement, our main tools are Gong and LevelJump. Outside of software, it’s important to have a sales methodology you are implementing across the sales team at the rep level to make sales training consistent and efficient. 

With all of this tooling, there’s a lot more activity that a single rep can do now than just five years ago. I believe companies are going to be able to sell more with fewer and fewer reps as more optimization tools continue to emerge. 

What is a reasonable budget for a series A stage company to set aside for this tooling?

I would say founders should budget anywhere from $10-17k annually per sales rep in sales software spend. That will include a CRM license, analytics software license, and sales optimization technologies like Outreach, LinkedIn Navigator, Connect & Sell, note taking apps, Gong, etc. There wasn’t as much to buy seven years ago when I started at NS1, but it is exciting to see what the toolkit looks like today.

Would you recommend that founders implement some of these tools when they are still doing founder-led sales? When is the right time?

What I found is that in founder-led sales, oftentimes the founder does the outreach and the first call, but they aren’t always great at the follow up. Founders often say they had a great conversation with a potential customer, and then when asked what happened it all gets messy. They get busy with their other responsibilities and never follow up. This is why sales people are hired, but could also be the reason that you adopt your first piece of sales software. Both people and software can be helpful from the start to put barriers of discipline in place.

When should companies start thinking about hiring sales ops people? What are some of the specific pain points that teams will start to feel? 

I would hire a sales ops person as soon as you’ve done your first, roughly, 5 to 10 deals and it’s pretty clear that there’s at least some product market fit. Once you get these deals under your belt, you want to start collecting analytics around the sales cycle and get detailed with your waterfall metrics from converting a lead to closed won deal. You’ll need to start building some structure so you can effectively add more Sales people and it will also give Marketing a good place to start from once you make your first marketing hires.

Something particularly important to call out for early stage companies is it’s super important to know your waterfall metrics when trying to raise a Series A, and especially a Series B. I wasn’t a tools geek coming into the role, and looking back if I’d hired sales ops sooner in the business, I would have been able to get all the analytics our founders needed to raise money a lot faster.

In your early funding rounds and budgets you may want to include not just your first sales hire but your first sales ops hire as well.

How might sales teams look different in five years compared to today?

Early on at NS1, seven years ago now, it was very difficult to connect with people on cold calling – the cold call rates were not good. I found that email and personal messages through LinkedIn messenger were a lot more successful. About two years ago though, I noticed that we were seeing lower response rates through these kinds of digital mediums of communication, and the cold calling rates started having a little bit higher success rates. 

I think we may be getting to a point where there’s a little too much automation technology. The human touch is really critical. Something that we did here that was effective early on when selling was we really nailed down our ideal customer profile (ICP). By doing this we were able to narrow our focus and spend time with the most likely adopters of our technology. Not only was it easier to prospect into a focused set of accounts and start conversations, but we spent a ton of time with the right customers in person, building credibility and thought leadership in our space. Ultimately it helped us build and deliver solutions our ICP’s found impactful. For example, we spent a lot of time hosting intimate dinners and creating an ecosystem of key individuals around us. Building that credibility takes time and you may not be able to sell to them in the short term, but over time we sold to pretty much all of these companies. You want to be pursuing the channels that other people are not, where there is less noise and typically less technology, too. 

Perhaps this means that the next generation of sales tools will be less focused on automation and more focused on making it easier to have real, old-school human interactions.

If you are building something in this area, please reach out to We would love to hear from you!

Check out other posts from the operator interview series:

Quirks and Opportunities in the LATAM Fintech Ecosystem

The Future of Telehealth is in Youth

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