Insights from Director of Sales Ops, Ian Stuart

Processed with VSCO with a6 preset

Riskalyze empowers its investors to make smart decisions by creating portfolios that match their clients’ risk tolerances. 

Ian Stuart empowers his sales teams at Riskalyze by creating the right systems, processes, methodology, and data to achieve their objectives. 

The two entities have the same goal– to be a multiplier and help their people win. 

When Ian and I connected (Ian in California, me in Utah), I could hear some rustling and static on the other end of the line. “Sorry,” Ian explained, “Our other building had a fire scare, I think it was an old vent. Everyone’s moving into this building right now.” 

Ian took my call when they were dealing with a potential fire.

“So let’s get started!” he said. 

I was astonished at his level of calm. But then I realized, this is a person who puts out professional fires every day. In this post, we hope to share a few insights from Ian that might “kindle” some sales ops improvements at your company.

Q: What do you find most difficult in your current role, and what is the most exciting?

A difficult part is having patience. Sometimes walking people through things multiple times is hard– so it’s important for things to be simple. Enablement is very important. On the flip side, my job is fast-paced–I like that a lot. I honestly love it. I like making things simpler, easier, not over-automating but making things more efficient… Tech moves crazy fast and there are always ways to make things more efficient and make the salesperson a little bit smarter. I like making my own systems easier. That’s why I like using Spiff… It’s really fast, it’s simple, it’s easy to use.

Q: What are the biggest sales ops trends you see?

Currently, in the industry, I think we’re getting to a point where we need to make sure the processes don’t undermine the reporting. Sometimes things get put together inefficiently. I think the right process will provide the right reporting. For example, get down to one way to log a call, and your reporting will be more accurate. Make sure there is one way to track information and require that from the reps. With this standardizing, you’ll clean up processes and provide a lot of transparency for your team. We’re currently working on what we dubbed “Project Thanos.” We’re going through Salesforce and making one way to do things as we integrate it with Spiff. Spiff shows a rep exactly where they’re at, whereas before they didn’t have a lot of visibility. They had some visibility, but this tool will help us explain what they’re going to get for each deal. 

Q: Speaking of deals, what kinds of incentive compensation plans do you use?

At the startup stage, plans should be evaluated often. You need to evaluate pretty regularly because the needs change as you scale up. I’ve been in sales ops for four years and I’ve seen companies not change their compensation plans after time… and they end up overpaying employees and they’re not profitable. Also, simplicity doesn’t always work out well. When comp plans are simple, they don’t let you get specific. I try to be specific so that reps are compensated on the exact metric the company needs… When you’re retroactively re-rating everything it’s less incentivizing. It’s effective to ramp up how much you’re accelerating at different tiers. That being said, have a plan that can scale. Monthly plans are a terrible idea financially. You’ll get a rep that gets overpaid for the year without achieving their annual target.  

If you need more quality appointments, define what that looks like and pay the rep when that happens. Pick the top persona you want people to target. By incentivizing exactly what you want, I promise you the reps will show up and do it.

Q: How do you present a compensation plan? What is most important to get your reps’ buy-in?

I try to grow the comp plan as we grow the sales team. You don’t want to make a plan that’s worse for the team. But when you do present a new plan for the team, it’s important to own the plan. Beforehand, get with the sales leaders and involve them in the planning process. I try to get someone brand new, someone in the middle, and a seasoned person to try to hack the plan. Then I get the plan peer-reviewed, or I’ll show it to a mentor or show it to a beta team/advisory team so that it’s not a surprise when it’s time to present the plan to the sales team. Afterward, I’ll have managers give me feedback. 

Q: Finally, with your experience in Sales Ops, what are some key takeaways that you’ve learned?

  1. Treat your employees like customers, one hundred percent. They’re not always going to know what’s right, and they’re going to think they need things that they don’t need. You have to know how to help them. I’m responsible for helping them win.
  2. You need to know their workflow in and out. You need to be actually in the team, on the floor with them. We instituted a flex desk policy so I can hang out with them all day and it’s been so effective to physically be there. 
  3. Prioritize transparency–it will go a long way. If you’re building a process, make sure that you don’t undermine your reporting. If you’re evaluating a result, first look at the process, the tools they’re using, and look at the people themselves. Rarely is a team missing their number because of what they did, it’s normally because of a breakdown in process or systems. That’s one of the reasons I love Spiff. Spiff is, by far,  the easiest thing to set up. It’s crazy complex but it doesn’t look complex… Spiff looks as approachable as a Honda Civic but it has a Ferrari under the hood. It’s really solid. That has been key in our reporting and data. 
Madi Bullock

Madi Bullock

Madison is a content, branding and PR expert. She currently works as the Director of Public Relations at Weave, one of the Top 100 Fastest Growing Saas Companies. Madi currently leads Spiff's content development.