Interview with Jessie Schreiber, Director of Sales Operations, Program Management, Ibotta

11 min read

Jessie Schreiber started out at Ibotta as an intern, unaware of the existence of sales operations. But with a passion for solving problems, Jessie says she was destined to get into the field. Sure enough, she’s now driving success at Ibotta as Director of Sales Operations. I was interested to hear more about Jessie’s close relationship with sales enablement and how they work together on specific projects. Jessie also told me about her onboarding process, measuring success in sales ops, and how to take tools away from the sales team as smoothly as possible. After giving me a rundown of her role at Ibotta, the interview began…

Rory Brown (RB): Can you tell us about your role at Ibotta?

Jessie Schreiber (JS): My role at Ibotta encompasses standard sales ops functions like vendor contract management, tool and system enhancements and partnering with sales enablement and other teams to help with their initiatives such as commissions, quota setting, account transitions. I also manage our project management office here and I manage a few of our resources on the Salesforce team as well.

RB: Great, thanks for that. How did you make your way into sales operations?

JS: I didn’t know it existed until about 4 years ago. I first joined Ibotta as an intern after college. I was on the account management path when along the way, I discovered I didn’t want to be 100% client-facing.  Instead, I was interested in solving internal problems, so I went down the more technical account manager route. I think I was destined to get into sales ops because my boss is an operations guru with 20 years of experience. When I started working with him, I started thinking very differently and saw a huge gap at the organisation. He had it in his head all along and jumped when there was an opportune moment to introduce both sales operations and sales enablement.  

RB:  Brilliant. And what title do you report into?

JS: I report to the SVP of operations. 

RB: Since you’ve mentioned sales enablement, it would be great to start by talking about how sales ops and enablement support each other, and where one stops and the other begins.

JS: From what I have observed in connecting with other people in Denver working for similar sized companies is that sales enablement is often a part of the larger sales operations group. That just isn’t the case here, and part of the reason for that is because of my boss and his specialisation. So we split them out. So far, it’s been working well for us, possibly because the way my mind works and the way the Director of Sales Enablement works. Her background is very heavy in Analytics. She is constantly looking for ways to make enhancements and tighten things up across the sales organisation. Whereas I am really the implementer. For example, she could come to me saying, ‘We need a better way to forecast this or that’ or ‘determine where the white space is.’ And my team is responsible for configuring and building tools to support those outputs, and often handing off reports for her team to use.

So the two teams work very well together. But I can see how there could be conflict in other organisations. It just depends on how much control somebody needs in their role. There is definitely potential for a lot of crossover. We have just been fortunate in that I am much more of a technical type of doer and she is the strategic ‘mind’ behind a lot of what is going on.

If I spot something interesting, I will take my finding to her to assess whether she wants to look into it further and implement a solution.

One initiative that we partnered on recently was putting together a compliance list for the sales and account management teams. For the most part, their variable compensation is based on quantitative metrics but there is also a qualitative component. What the Sales Enablement leader and I have been able to enforce is accurate and timely data entry to capture client touchpoints, mostly within Salesforce. It took four months for us to ensure all of the things could be done in the system. Now we have rolled it out and this is the first quarter where if people will be rewarded for meeting the criteria. And even better, the Sales leadership can find coaching opportunities at every stage in the sales funnel.

RB: Great. Coming back to what you mentioned before about spotting something interesting and taking your finding to your sales enablement counterpart. When you talk about spotting something, what are you typically looking at?

JS: I get a lot of satisfaction from poking around the data. For example, I have reports sent to me on a weekly basis for this very specific fee that we charge on a lot of our programmes. And I might go through that list and take a look at who has been waiving the fee consistently versus who is collecting the fee. Just as much as I want to surface the people who aren’t pulling their weight, I want to surface the ones who are going above and beyond. So I will take opportunities to look and say, ‘Bob seems to really understand how to sell this in at the full rate. Maybe here is an opportunity for him to do a teach-out to the rest of the team.’

On the other side, perhaps people aren’t logging into specific tools or leveraging automations that we use in our sales engagement platforms. Often, these tasks are perceived as ‘busy work’ by the sales team. We are starting to make some changes to help them understand the benefits, but occasionally we have to be the bad guys and figure out where there are holes. 

RB: I really like the framework that you touched upon: You look, you see the range of different behaviours among the sales team, and then enablement comes in. Do you use this framework a lot? 

JS: Absolutely. The sales team does a good job of that on their own. But the Director of Sales Enablement and I complement them in uncovering things that aren’t visible on the surface. We’re constantly looking for those outlier behaviors. It is also just a great way for them to get visibility. Sales people want credit for their work. And conversely, they won’t enjoy being called out for poor performance or counterproductive behaviour. We need to uncover that behaviour so we can teach it out in a positive light, where their good work has tangible rewards.

RB: I like this concept of ‘teach-out’. Could you talk me through that?

JS: We have a lot of stand-ups around here. Every Monday morning our Consumer Packaged Goods Team, which is about 60-70 people, has their stand-up. The format is: Updates from the team leads about big wins (deals, innovations, projects) and there is typically a short presentation given by two people. One of them a salesperson and the other, their counterpart from account management. They present on topics relevant and valuable for that 60-70 person audience. Possibly a break-through with a new account, or how they turned a negative client experience into a stronger partnership.

We have a lot of opportunities to do teach-outs and our culture promotes good ideas coming from anywhere (one of our company values since day 1). Consequently, people feel they can take some risks and this of course results in some really exciting ideas coming up from the person you least expect.

Our sales enablement group just hired a tools instructor, who will be responsible for start to finish, top to bottom of sales funnel training on what buttons to push, in what system, by what role, at what time.

We are in the trenches of building a lasting solution for training and instruction because in the past, admittedly, it has been a scrappy ‘just get it done’ approach.  And of course, we see a lot of variability depending on what sales leader someone has, they often have a completely different onboarding and training experience from their neighbour. I like the sessions where people have an opportunity to do a teach-out with the entire group, so regardless of who their boss is, they are learning some type of skill or information in one setting.

RB: Brilliant. So the notion is that the ideas you and sales enablement implement can come from anywhere. You are promoting that culture.

JS: I’ve been surprised. Some of the people who come to us with the best ideas are 23 and 24 year olds. They come in with a fresh set of eyes and question everything, for example, ‘Why am I entering information three times?’

We really value that. And there are so many means of communication to share ideas. My team is open to receiving feedback or ideas through Slack, email, or even people stopping by their desk. We have an open desk plan and they are definitely encouraged to raise their hand – within reason, of course.

RB: Nice. I’m interested in this tools instructor role too. When did that come about? 

JS: He moved into the role about three weeks ago. Before that he was the trainer for one specific group and now they have broadened it to be all of Client Partnerships, Client Success and some Operations groups. Everything from outreach/prospecting tools, lead generation tools, Salesforce, you name it. He will be the go-to resource for what tools and processes they will be using, how to use them, and how to provide related feedback. Then he will work closely with my team. The Salesforce resources know the platform better, so they are who you turn to for why things are happening.

RB: Yes. Brilliant. If we take onboarding, which is typically seen as a sales enablement initiative, what would you say in your experience is sales ops’ role in the three months?

JS: Onboarding has been slightly messy here but we are beginning to implement more structure around it. I do intros with new team members to give them a run down of how my team operates and how we can support them. And from there we have office hours for the Salesforce team, where they spend an hour with them learning about how and why we use it. They also sit with sales enablement to learn about their function.

The onboarding process needs some improvement. We don’t have tons of people starting at any given time, so it is not unmanageable, but we are trying to get to a healthier place and I think having that tools instructor is really the foundation. It means that my team and I don’t end up spending way too much time training someone before it is relevant for them. It gets them selling and managing accounts more quickly.

RB: Great. That reminds me of my interview with Marissa White, Founder of Sales Ops Help who shared the details of her ‘just in time’ onboarding. You train someone on a tool or process the moment before they are about to use it. So as they go through the journey of the sales process, they get their pipeline further and further.

JS: Yes. It makes perfect sense because they sit in trainings right now, nod their head, take a crazy amount of notes, walk away and retain none of it.

One thing that I encourage my team to do is let them go into the tool themselves and interact with it rather than having them watch a presentation or read a one-pager. Click buttons, find your own way to navigate the platforms.

RB: Brilliant. Moving onto forecasting, you mentioned earlier that your sales enablement counterpart said forecasting needs to be more accurate, which is often an initiative from the sales ops angle. So I’m interested in how that dynamic works. In that particular example, why was forecasting brought to your attention by your enablement counterpart?

JS: This is something that I have been thinking about for a while, but it hasn’t been as critical to my role. One of the reasons it was important for her is that she entered the company and realized that we had a lot of issues with forecasting and quota attainment versus what we had actually set and predicted. It is not to say we had people sandbagging their quotas necessarily, but we were struggling to keep the appropriate percentage of our sales people within 75% – 125% of their quota, and we were having a difficult time forecasting what these accounts would produce.

RB: Yes, great. Moving onto a slightly broader topic, how do you measure success in sales ops? What has been your experience of that?

JS: It is challenging. During my first year in this role I had more flexibility because we were aiming to just get sales operations settled in as part of everyday life here, which we accomplished. Again, my team is unique and I benefit from that from a KPI and metric perspective because I have Salesforce work and project management, which are more measurable.

A lot of what we are looking at is specific to our company and relates to transforming the way that the sales and account management teams do their everyday work. That comes from efficiencies gained, data accuracy, and building scalable business processes and tool solutions.

Sales enablement and sales ops sometimes have shared goals. One of them recently is something that is more industry standard. We needed to see the appropriate percentage of opportunities in Salesforce go through each of the stages, because in the past everything had been going in at ‘verbal accept’. So we had no pipeline visibility.

We set a very specific goal. If we had seen that only X% of opportunities sat in stage 2 previously, and for how long, we went in and applied specific percentages to drive a Y% increase, so that the sales managers were able to see all the opportunities throughout the entire funnel.

Here is another broader example. We are trying to make Salesforce a single data entry point solution for all revenue generating activities. In the past, we had a different system that we call “Admin” (customized administration interface on Rails), which we are now transitioning out of. Both of them now are technically active, but I’m trying to move everyone out of the old one. Part of that was looking at how many of our campaigns get initiated in Salesforce and then pushed to the other – versus created in “Admin.” Those are obviously very tangible and specific tools in the stage that our company is at.

For me professionally, my boss and I have a great relationship and trusts me. A lot of what I’m measured against is feedback from all of the teams that I’m working with, related to what tools I implement, what tools I take away and enhancements my team drives.

We can gather that sort of per and team feedback via survey at mid year and end of year.

RB: Brilliant. That is a very good answer.

You talked about tools and the fact that you have taken tools away. On the blog, we’ve had a lot of discussing around implementing tools and the process around that, but actually, the converse is quite interesting. What drives you to take a tool away? And how do you deal with the fallout if people liked the tool? 

JS: I am actually starting an initiative to take one away – we’ll call it “tool A.” Tool A worked 5 years ago, but we have outgrown it. I am in the early stages of deprecating it and introducing a different tool, “Tool B” that has everything “Tool A” has, plus much better reporting functionality. Some people won’t be happy initially, but it’s only because it represents change, uncertainty and a few hours of extra work up front.

I will give you another specific example where we transitioned from Yesware (the Inbox point solution) to Outreach, which is a more fully baked sales engagement platform. If I had to go back, I probably would have re-signed for at least a year with Yesware. 

We knew the team didn’t love Yesware – it was plain, simple, and we consistently experienced technical issues with the Chrome extension. But the key to that was, it was simple. So I had a sizable group of people across all teams, across all roles, and we went through a pretty deep-dive into vetting Outreach and their other competitors in the space. 

I had created surveys, they evaluated, and I created a thorough competitive analysis that was reviewed by sales leadership. Outreach came on top but for a lot of the wrong reasons. That didn’t get discovered until after we tried to implement it and the complexity became apparent. Testers liked the user interface during the buying process but that shouldn’t have driven our decision. The product was built for SaaS companies that handle high volumes of prospecting and need all the bells and whistles and sequences. We don’t, we need something simple that provides specific value without keeping our teams from their actual selling activities.

I have learned some valuable lessons about what to look for, and what feedback does and does not matter. In some instances, I can objectively say that the way that people are using something is not how it was intended to be used.

“Tool A” is not meant to be used for someone’s personal task list. So if people come to me saying “I can’t do my job without it,” I hear them out, but am ready to explain exactly how “Tool B” is going to be a better version of that task list, plus more.  I prepare for those conversations ahead of time.

RB: That is a really good example. Thank you for that.

Want to get more insights from sales ops leaders? Check out our other posts in the sales ops interview series.

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