What makes a great leader in martech sales? The yardstick I have always used is the ability to scale a successful team by attracting, and getting the best out of, the most talented professionals in the market.

For that reason, I hold Tod Klubnik in the very highest regard. His success as a head of sales, and latterly a CRO, at SaaS businesses made him a natural fit for the first episode of The Martalks Podcast.

I wanted to know his secrets in scaling teams. What are the mistakes to avoid? How do you bring a product to market? And what are the steps you need to take in graduating from selling to SMBs and mid-market businesses, to enterprise scale organizations?

You can listen to the full podcast using the embedded player here, or continue reading for our summary of Tod’s insights.

Building a superstar sales team

In his role as Head of Sales at MessageOne, Klubnik scaled his sales team to brilliant success. Before he joined the company, the team hadn’t secured one deal above $500k. When he left, they had billed several deals worth over $7m. What are the steps to achieve that success? Based on our discussion, I’d break it down into three steps:

  • Starting out with a best in class company executive attract the very best personnel available
  • Trusting your sales leader to hire and implement processes
  • Creating a robust training programme to expand your team’s product knowledge

In some cases, ‘starting with the right leadership’ is a chicken-and-egg situation; few founders replace themselves. But Tod explains that there is a widespread problem of startups making stopgap hires. Startups are often built around the founder’s immediate networks of a founder, which frequently leads to unsuitable people end up leading crucial revenue functions

If your scaleup looks like a mom and pop operation because – in Tod’s words – “someone’s husband is running marketing when they aren’t qualified”, it will be almost impossible to lure the premium talent you’ll need to grow.

As Klubnik puts it, “talent attracts talent”. That starts by building a premium executive team that attracts the very best in the market.

It really starts with putting together and committing to a great executive leadership team that has a great culture and is very collaborative, where everybody respects each other and there’s no glaring holes.”

In my experience, the best sales guys are fleet of foot, and unlikely to join, or stick around at a company with preexisting leadership problems. But with a trusted lieutenant as a head or VP of sales, the table is set to build a team that can scale and grow at pace.

Startup founders and CEOs often wait too long to make this step. I mentioned this on our previous blog: ‘Martech scaleups: how to hire a VP of sales’. In a startup’s infancy, founders often lead sales. Their understanding of the product and their passion make them the best advocates in those first couple of deals – but this eventually proves unsustainable. There are too many other strategic decisions they need to be across to closely lead the hiring of a new sales team. Klubnik says that failing to appoint the right trusted lieutenant to take over is all too common.

“I’d say the [biggest mistake] is not getting the right sales leadership team in place from the beginning. One of the huge benefits of that is they can help you recruit, they can help you vet and really help you scale that team quickly versus feeling like you’re trying to do it all yourself. And I’ve made that mistake before.”

Once a trusted sales leader is in situ, it’s their job to take control of the sales process, and indeed the hiring process of sales reps, to create a function that has the autonomy and the processes to grow. Klubnik sees the role of the CEO in sales from that point as being a strategic overseer, who can be dropped in to get business critical deals over the line.

“For a CEO to properly set strategy and be a great leader they have to stay connected, but they have to be willing to let the sales leader do their job. Whenever it’s not happening, you have to speak up, and you have to push back and explain… you hired me for a reason.

“They go on calls, you pull them into big strategic deals, they, do peer-level executive to executive selling, but…they can’t own all the daily decisions that are happening.

“That’s inevitably a point of friction in many companies, and it’s just part of the growing process.”

As to who you hire: it’s important that they have the background in selling to a similar profile of client. This is especially important in martech, where the industry is trending towards a greater number of microservice solutions that are optimized to fulfil a particular function, or serve a particular industry. The ability to source and build relationships based on profile is the type of skill that can translate across SaaS, but familiarity of pain points and specific client goals breaks down quickly from one solution to another

As Klubnik points out, knowledge of product is developed over time, but the time required to train sales skills isn’t necessarily one a fledgling martech company can afford.

“We can teach them a new product, they can learn a new industry, but if they’ve never done deals over 50k, and you’re going to put them in enterprise sales, doing half a million to $2 million deals? There’s going to be a steep learning curve.

“When you’re scaling sales teams, you don’t have time to have somebody learn a new role, and a new product and industry at the same time. It’s much easier if they can be plug and play in terms of the role and the type of selling that they’ll be doing.

What can and must be trained effectively, however, are the company’s own sales process and product knowledge. The retention of staff depends on a company’s ability to provide on the job training and build an effective cohesive unit – something Klubnik says most software scaleups are “terrible” at.

He cites the example of both his work at MessageOne, and BigCommerce of how a rigorous training programme can help deliver for growing sales teams. At both businesses, he helped build a suite of videos, roleplay scenarios and assessments that drilled staff and gave them intrinsic knowledge of the respective products.

This doesn’t need to be overly complicated; it needs to be rigorous, and reflect real life scenarios as much as possible.

“At the end of every two weeks, we would do a little roleplay, whether it’s a prospecting call, or giving a presentation or doing competitive differentiation… and assess how they’re doing, I’d rather have them fail within our four walls than out there.”

Going to market: a joint effort between marketing and sales

One of the most frequently-asked questions around go-to-market (GTM) strategy is whether it should be owned by marketing or sales. Tod describes the idea that it should be owned by one or the other as a “fallacy”.

It’s a trap. It has to be jointly owned… I see in so many companies they say: ‘sales should own it’ or ‘marketing should own it’. Inevitably, they just butt heads. There’s a power struggle and egos and hurt feelings due to these silos.

During his tenure at BigCommerce, Klubnik built a unified GTM team featuring personnel from both sales and marketing. That joint effort meant that the two functions were in lockstep, working towards a shared idea of the crucial first impression of their product.

“We did everything together. Weekly meetings, sales and marketing kickoff etc. We had one strategy, we were attached on the hip on everything. We each owned our own elements, but it was the one team with an overarching strategy.”

Critical to this strategy is nailing down your product’s most important value selling points.

This process should be led by the GTM team members that have the most experience in your product’s specific niche. Their understanding of your clients wants and needs will help to draw out the USPs of your proposition.

Those differentiators need to be front and center in every touchpoint of your client’s lifecycle; requiring complete synergy between your marketing, sales, and customer success teams. Klubnik admits this is a difficult job, but you can make crucial gains by prioritizing a subset of your most frequently used sales assets. This can be as complex or simple as your resources permit.

“Messaging and positioning exercises can be thousands of lines, and millions of dollars over many, many quarters. You don’t have the time. You do have the time to make sure you nail the most important value selling points, and your differentiation.”

“[Your selling points] has to be used in every single customer touchpoint across the customer lifecycle. That’s a prospecting call, a letter, cadences, presentations, demo scripts, marketing, messaging, website, case studies and so on… identify the five to seven sales assets that you use every single day and get those consistent and right. And you’ll move a lot of Earth just by doing that.”

Scaling from selling to SMBs to enterprise

A typical trajectory for a martech is to start out selling to SMBs, and then progress to enterprise targets.

During his time with BigCommerce, Klubnik’s sales team increased the share of enterprise business from 20% to 65% of total revenue. Again, I would segment his advice on scaling from SMBs to enterprise into three steps:

  • Ensuring that the strategy to sell to enterprises is a company-wide one; not just in sales
  • prioritizing customer success – building out the customer success function appropriately and making sure sales doesn’t oversell the product
  • hiring sales talent with experience in the enterprise market.

While sales will obviously play a huge role in going after enterprise targets, Klubnik advises that this decision lies with the top level executive team – since it largely comes down to proving the viability of the product.

“Your product has to be ready. The product has to be enterprise-scale, enterprise-ready, ready to handle all the things the larger customers need. It has to be able to compete with the entrenched players in the space.”

Going after these larger organizations invariably will require new hires, not just in sales but across your wider commercial team.

A customer success operation will be crucial for keeping your bigger clients happy, although it may not necessarily need to start out as a fully-fledged team.

“You don’t have to spend a tonne of money or over-hire for this, you can start by just hiring a great director-level person for customer success.”

Klubnik is also clear that the responsibility for customer success starts with marketing and sales accurately selling the product to the right demographic of clients. It’s then about creating a seamless process where those clients are handled with care for the entirety of their relationship with the business.

“Are [sales & marketing] focusing on and going after the right type of customers? Do they fit the right profile that’s going to be successful with the product, where we are doing a good job with discovery and identifying pain and positioning the value of the product… not overselling or stretching what the product can really do.

“A good handoff process between sales and CS is critical. Sales should stay involved for the first few months to make sure there’s a good transition.”

If marketing and sales outpace the rest of the business, it can have profoundly damaging effects. Without the right product, reaching out to bigger clients will cost the company thousands of dollars in wasted advertising spend, and possibly waste sales time that could be better used engaging with the established buyer profile.

Enterprises have needs which are not common to businesses of every size. Klubnik says this means you should hire sales talent with the experience of selling to these major players, while also updating customer success processes to cope with the increased number of users of your software.

“You have to have the services component in place. Your clients will expect strong consulting and training services, much more than small businesses and medium sized businesses. They’re willing to pay for it, but it’s got to be good and it’s got to be there.

“You have to hire the right profile of sales leaders, enterprise sales, reps, SEs, BDR, etc, who have success in selling to enterprises as well. One of the mistakes I see companies make is they take their mid market sales teams and say, ‘Okay now go sell to the enterprise’, or their mid market and SMB marketing teams say, ‘now let’s go market to the enterprise’. You need to complement those great teams that you [already] have with some outside talent that has been there and done it.”

Scaling a function is by no means a linear journey. Along the desired martech journey from SMBs and mid-market to enterprise, there is no one clear route to success.

Trusted colleagues move on to pastures new, the added bureaucracy of large organizations can slow down your processes, the demands of your customers and clients change. Your sales leader needs to be unflappable throughout these ups and downs, all while fostering a culture that allows others to thrive.

Throughout our conversation Tod was quick to put the focus back on the teams he assembled at businesses like BigCommerce and MessageOne. A consummate leader to the end.

I would posit the theory though that this humility is one of the traits that brought him success. It’s the type of behavior that builds a winning culture, and attracts premium talent. And as Tod put it himself: “talent attracts talent.”

Search for your next sales leader with Rosenstein Group

Rosenstein Group has over 20 years’ experience as a leading executive search firm in martech, ecommerce & supply chain SaaS. We’ve recruited heads of sales, marketing leaders, and other members of the commercial team at businesses of all sizes: from new startups, to enterprises such as Salesforce, Demandware and SAP Hybris.

Learn more about our service specialism in martech here.

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