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Sales Leader Interview Series – Liz Cain

Data and Experimentation: The Modern Sales Manager

Liz Cain is an experienced leader and venture capitalist with a background in sales and sales operations. She is currently a partner at OpenView, a noted enterprise software VC fund. Before that, she held a variety of sales and management positions at NetSuite, culminating in a role as AVP of WW Business Development where she grew her organization from 0 to 170 people over four years. 

We sat down with Liz to discuss the responsibilities of a sales manager, transitioning to remote operations, and incorporating new segments into a sales team’s target market.

How do you think the current transition to entirely remote selling will impact B2B sales going forward?

I keep coming back to how adaptable human beings are in general. We learn to get comfortable with almost anything given time; think about the evolution of software sales from the huge, face-to-face enterprise deals to the now very frequent self-serve, bottoms-up sale. 

I think people are getting more comfortable buying over the phone, and buying across industries, verticals, and departments. We were already seeing a trend emerge where there was more selling being done over the phone or via online self-serve, and I think the current environment pushed that trend forward. 

I’ve thought a lot about how this crisis changes a true enterprise field sales motion, and the things that I keep coming back to are implementation and customer success, rather than actual selling. I think the selling will adapt faster, and where we’re going to see some challenges is in figuring out how to do some of these deployments that usually require a lot of in-person training.

How do you recommend sales teams think about experimenting with new segments?

We’re seeing a lot of companies pivot and try to do more self-service. We’re seeing other companies try new, creative approaches to their go-to-market. I don’t think there’s a one-size-fits-all type of answer for this, but I do think that great ideas come from within different parts of an organisation. So, make sure you’re soliciting that feedback and there is an avenue for people to bring good ideas forward. 

Secondly, there’s the question of prioritisation, and figuring out how you’re going to measure and understand impact. A lot of the experimentation I see makes it very hard to associate causality. If you make three changes at once, how do you know which thing is working?  You can do this in a couple of ways: you can either set up really clear measurements and a defined time period, or you can break off part of the team. No matter the type of experiment you’re running, my one piece of advice for people is to make sure that the sample size is greater than one. You need to have a couple of people doing it so you can really understand whether the idea is working broadly.

The last thing here is also thinking about how the experiment fits into the broader business plan, and understanding how big that impact could be. Is this a short-term change you’re experimenting with because of the current environment, or is this a large pivot that you’re making for the business? 

Where do you see a sales manager’s responsibility in generating data-driven insights?

The reality is that the sales manager is going to need to figure out how to deal with data. My real opinion, however, is that they actually shouldn’t be doing it. If you think about people leaning into their strengths, the average sales manager shouldn’t be running data. They should be on the phone, coaching reps, helping to close business. 

I guess in my ideal world, they are the customers of data. Yes, they need to understand how to interpret it, but they shouldn’t need to be able to pull it. Instead, they should be able to get an output and make a series of recommendations to their team based on it. So, to me it’s more like they’re the insight gap of what do you do once you know X, not how do you go find it. 

I think we are now creating unbelievable amounts of data that we did not used to have, and that people are not trained to look at. I tell every founder I talk to that sales ops/revenue ops/business ops is the most underrated job at a company, and when you find somebody who knows what to do with data, you can get some amazing insights. People shy away from it because it feels like a cost center, and they look at it as another expensive resource that isn’t quota bearing, but I actually think of it as a support mechanism that allows you to make better decisions and accelerate the performance of the team. 

What advice do you have for sales managers looking to become better coaches?

I think the biggest mistake people make is trying to coach too many things at once. Everybody always has things they can improve—no one is perfect—but coming at somebody with ten things they could work on is never helpful.

I think you also have to be really clear and consistent on what you’re coaching on. So, if you’re going to give feedback on a certain thing, make sure they’re clear on what your expectation is, what the bar is, or what change you’re trying to impact. 

Lastly, I think it’s important to separate “coaching” and “management” time, especially in a sales job. We have one-on-ones where we can talk about metrics, career path, or whatever is on the agenda that week, but make sure you actually set aside specific coaching time that doesn’t get buried by any other to-do-list items. I think it’s really easy to let it seep into everything else, and it just gets deprioritized.

Thanks for sitting down with us, Liz! We always enjoy speaking to people with interesting and informative perspectives on the sales world. Stay tuned next week for another post in our Sales Leader Interview Series, and check out the BuyerSight Blog for more great sales content!

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