How Cirrus Insights Co-Founder Brandon Bruce Still Finds Ways to Support His Sales Team After 7 Years

Collin Stewart, CEO

18 July 2018

Over the lifespan of a company, whether it be slow and steady climb or the lightning quick rocket ship ride of a unicorn, the role of the founder will invariably change.

At first, they do it all – marketing, sales, and customer success, for instance. From soup to nuts, the founder is the person executing on every last responsibility. If they’re good and, naturally, a bit lucky, their company will grow and others will come onboard to handle different roles and train subsequent hires on the ins and outs of the job.

It’s a beautiful thing, when it happens.

But although the new (and often amazing) people that join a team absorb the crushing workload initially shouldered by a founder, it’s up to that leader to evolve their role, and continually find ways to support their team.

Of course, that evolution is easier said than done. When you’re used to doing everything, having your hand in every decision and every deal, how do you let go?

What does this evolution actually look like?

“So, the question always is: as a co-founder, do I still sell? Am I still involved in sales? The answer is yes, and yes. I think that leadership should always be involved in sales. So, part of my role is sharing the good news of Cirrus Insight on blog posts and podcasts,” says Brandon Bruce, Co-Founder and Chief Operating Officer at Cirrus Insight, on a recent edition of The Predictable Revenue Podcast.

“Hopefully, from that sharing piece, they engage. So, there is a prospecting element to my job. And once there is engagement, I support. I don’t lead, for instance, the product demo, or negotiation, or security review, or legal review. But, I will be there to support sales, customer success, engineering – whoever is involved. So, from a high level there is a few things where I can add value by doing simple things. One of them is simply showing up.”

Supporting security needs

If you’re doing business in the European Union, or have clients that do business in the European Union, you’ve likely been wading through the new General Data Protection Regulation (GDPR) legislation put in place earlier this year.

(Editor’s note: in early June, we covered GDPR extensively. Check out our podcast on the legislation here, and a guest post from digital privacy expert Daniel Barber here.)  

At the moment, the sweeping privacy legislation has ramifications only in the EU. But companies across the world have taken notice, and many believe it is only a matter of time before new, and more strict, privacy laws appear in other jurisdictions. As such, Bruce has been fielding questions from both clients and prospects about the GDPR framework, and whether or not Cirrus Insight is compliant.

As is the case with any nuanced legislation, the devil’s in the details. And, as challenging as that can be, not knowing those details when called upon by a prospect can derail a sale. So, Bruce helps ensure everyone, customers and his own team, are kept up to date.  

“My role in this regard has been to get our ducks in a row, and be ready for GDPR. That can be preparing and presenting addendums etc. about what data we are processing and collecting,” says Bruce.

“We have gotten a lot of requests for information on GDPR, and we have tried to get ahead by getting that information out there. Compliance, risk mitigation, risk management – people are really paying attention to all of these factors. Sales is hard, the last thing you want to do is handicap them by not being ready for GDPR requirements. We need to anticipate that need, and be quick to respond.”

Legal reviews, a hallmark of the sales cycle, are another avenue of support Bruce provides. For example, if a prospect’s legal team – typically from a large company – suggests changes to Cirrus Insight’s Terms of Service, or demands using a contract they created in-house, it’s Bruce that reviews all of those proposed alterations.

That could mean simple adjustments such as font size, or deal-breaking requests such as a “termination for convenience” clause, in which a prospect stipulates they can walk away from a contract whenever they wish.

“That, in my opinion, is not okay. You can’t just walk if you want to walk,” says Bruce, a law school graduate.

“In that sense, it’s not okay to have that in the deal. After all the work such as a pilot, and customizations, that’s not a good start to a productive, long-term relationship.”

Handling procurement’s needs

As every seasoned sales rep will attest, navigating the procurement minefield is a must for most enterprise level deals. Unfortunately, the goal of a sales team and the goal of a procurement department are often at odds – procurement wants to pay as little as possible, while sales would prefer a prospect pay top dollar.

These opposite agendas can be a challenge, and also kill a deal if not handled appropriately. This is where Bruce’s experience handling all of those early deals on his own proves invaluable. He’s dealt with procurement, knows their language, and understands when to bend, and when to stand firm.

“Although, I love the folks that work in procurement, I have called them the anti-sales in the past. So, it is helpful in those situations, when more people are being brought to the table, that I can help in being an extra warm body,” says Bruce.

“I’ve dealt with procurement, and can share what I’ve heard in past. You have to know where to negotiate, where to hold firm, and how to proceed along the deal.”

A bit of advice

Having a C-level executive jump in a deal, at any point along the cycle, is a critical pillar of support to lean on. And it demonstrates to prospects that the company takes the deal seriously, and wants it to work for everyone involved. But, help goes both ways. Reps, adds Bruce, should feel comfortable to approach executives early on, describe the deal they are navigating, and ask for advice ahead of time.

Being prepared for anything that could come up – whether it be legal requirements, legislative effects, or procurement demands – will keep a deal on track.

Sharing their wealth of knowledge also keeps founders engaged, and on the frontlines. Remember, as those new team members come onboard, they start taking over (and making their own) many of the founder’s previous responsibilities. It’s up to the founder, then, to find different ways to support the team.

But jumping in the eye of the storm, at least from time to time, is still a rush.

“Part of the fun of starting a company is building the customer relationships, being part of the deal, and getting to feel the adrenaline of the deal. It’s exciting,” says Bruce.

“I encourage founders to keep doing that, to stay in the game.”

For more on Bruce’s methods and tactics for supporting his sales team, check out his full interview on a recent edition of The Predictable Revenue Podcast.