Out-Hustle Yesterday: Marketing Hour by Hour With Ibotta

Editor’s Note: This newest installment of the “Marketer Spotlight” series features Derek Cann, marketing automation manager at Ibotta. Read on for his daily schedule (you may want to pencil in a day to try it!), his martech stack, and more.

If you’d like to be featured, email [email protected].

Can you tell us about your typical day at the office?

When you speak to most marketers, you get the impression that every workday is like jazz, in which they occupy a space of improvised, free-flowing artistic journey of creative exploration. My work day is the opposite of that. I’m a process oriented planner who organizes my time around my own predictable mental patterns. I am better at different types of work at specific times in the day.

“Out-hustle” is an Ibotta core value that I take to heart. Every day, I seek to out-hustle competitors, other marketers, and my best self from yesterday.

One thing I have in common with every other marketing professional is the need to wear many hats throughout the day to be successful. In the course of a day I move between the roles of strategist, people manager, product manager, project manager, individual contributor, and analyst. Here is what what a typical day might look like:

7:00–10:00 Creative mornings: Mornings are made for coffee and independent creative work. This is the time to overdose on caffeine, turn up the headphones, and crank out any work that requires creative solutions.



10:00–12:00 Manage ongoing projects and direction set: This is time to answer any emails that arrive early in the morning and to meet with my team to make sure that ongoing projects and priorities are on task and moving forward, free from blockers or unexpected hurdles.



12:00–1:00 Exercise, meditation, and lunch: This combo in this exact order beats that midday coffee and recharges me to crush the second half of the day.



1:00–3:30 Product integration and strategy: I am my most strategic and focused self at this time of day. As a marketing automation manager on a user retention team, my role is a very collaborative and cross functional. I reserve this time to draw up detailed strategic plans and work with our product team on any key partner-integration projects.



3:30–5:00 Performance analysis, reporting, and industry education: This section regularly overlaps the previous time slot, particularly when I am working on projects that require data-driven decision making. I believe that it is important to set time aside to read industry news and reports, take vendor calls, listen to podcasts, and keep up with reporting.



5:00–6:00 End-of-day wrap up: Work-life balance is very important to me. I am a firm believer in my version of inbox zero. I spend the end of my day answering any outstanding emails, comments on projects, and tying up any ongoing project conversations with team members.

What is your greatest challenge and opportunity as a retention marketer?

Building data-driven, lifecycle-marketing campaigns that are personalized to each user is both our greatest challenge and biggest opportunity. The challenge is not a lack of data, but how we leverage our wealth of information to create personal, predictive, relevant, and timely 1:1 marketing programs. The challenge is huge, but the payoff will be happier users with improved retention rates.

What skills are most important to succeed in retention marketing?

To retain users, marketers must take a user- and data-centric approach to every problem that they seek to solve or metric they wish to improve. It’s incredibly important for junior marketers in particular to learn how to test into solving problems that cannot be answered with a Google search or learned in a classroom. An MBA is a great first step, but education alone does not make you a marketing professional. That skill is developed through years of testing, analyzing results, and repeating that process on a varied set of challenges.

This was a lesson learned the hard way early in my career. The day I began truly letting the data drive my assumptions, planning, and winning variant selection brought me both reduced anxiety and validation. I learned early on that a beautifully executed, strategically sound campaign may fail. Sometimes that ugly email that has been around forever really is the best way to activate and retain users. My takeaway, which has forever improved my approach, is to let the data tell the story; do not use data selectively to craft the story you want to tell.

What is unique about your approach to retention marketing and how does mobile fit into that?

I refuse to rest on the laurels of a winning campaign. If a campaign succeeds, it becomes the new control to test against with challenger iterations.

Mobile sits at the center of every campaign we run. We’ve quantified the average value of each message type we use (in-app message, email, and push) and the incremental value of stacking each of those message types. As a result, we approach our campaigns starting with mobile messages and then building outward into email to increase reach and support the other channels.

What tools and technologies do you most rely on to do your job?

Appboy powers nearly all of our retention-marketing communications. It’s backed by our internal data tools and an owned GEO infrastructure. We use Pivotal Tracker for product-and-development–related project management, and Trello to manage creative requests.

Which teams within and outside marketing do you most work with?

I work regularly with the product-development, customer-support, and technical-account-management teams. Staying aligned with these teams is critical to taking advantage of Appboy’s total feature set, which includes handling customer feedback, aligning our multivariate marketing tests with our app offering, and maintaining consistent in-app communications.

What’s your marketing mantra?

Always be testing.

Aside from your own, what brand’s marketing campaigns or messages do you love most, and why?

Airbnb is killing it. Their recent “Live There” campaign that encouraged travelers to “live like locals” was brilliant. The spots challenged the traditional traveler to not simply land, check into a standard hotel, and “do Paris.” Instead, the campaign encouraged travelers to have a richer, more meaningful connection with their host community.

More specific to marketing retention, I am really impressed with the meditation app Headspace. Their messaging is highly personalized, relevant, and timely. From the outside looking in, it appears that they leverage usage patterns to predict a user’s likelihood of maintaining an established meditation practice. If a user starts to fall off, they’re quick to send goal reminders, celebrate historical achievements, and trigger general messages supporting the benefits of meditation. They also send up to five really solid push notifications a day reminding the user to maintain mindfulness.

What are some of the most important drivers for the campaigns you make; are they based around customer events, purchase behavior, seasonal promotions, new store openings…or what else?

The campaigns I oversee are all lifecycle centric, based on activation events, preference and engagement attributes, purchase behavior, and account age.

What gut checks do you go through when designing a campaign, from ideation to launch?

I have more of a formalized process than “gut checks.” I start by evaluating the metric we are looking to improve. Then ask a series of questions:

1. “Is this the right message to achieve the goal?”
2. “Is the message relevant, timely, and personalized?”
3. “How would we test against this approach in the next campaign iteration if this first campaign is successful?”
4. “Can we leapfrog to a more impactful execution with a small amount of time investment?”

We then build multiple versions of the campaign, putting each touchpoint through a formalized team-feedback round and quality-control process to ensure that each element is free of errors, triggering properly, and set up to accurately measure performance.