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Host Callan Harrington dives into the strategies, decisions, and lessons that have shaped the careers of top marketing and growth leaders in the insurance industry. From bold moves to costly mistakes, each episode uncovers real-world insights that listeners can apply to accelerate growth in their own businesses.
Amber Wuollet 00:00
How much do we need to sell of this policy for it to be a success? So that you are setting yourself up to know how it is going, so you can iterate as needed. So we aligned on a goal and implemented new messaging, new positioning, and, of course, new assets. And we blew our goal out of the water. We had a 12 month goal, and we hit that in about six months.
Callan Harrington 00:23
Welcome to the Insurance Growth Lab, where we go deep on the growth campaigns and strategies driving real results in the insurance industry. I am Callan Harrington, founder of FlashGrowth, and in each episode, I sit down with marketing and growth leaders from carriers, insurtech, and top brokers to break down one specific initiative, whether it is how they marketed a product, scaled a channel, or solved a specific growth challenge. It is no fluff, just tactical insights you can apply in your own company.
Welcome back everyone to the Insurance Growth Lab. I am Callan Harrington, and today I am joined by Amber Wuollet. Amber is the Director of Product and Lifecycle Marketing at Cowbell, and she is an insurance vet. I was lucky enough to work with Amber during my time at Bold Penguin, and we actually kick this episode off with one of my favorite stories, not only from our time together, but of all time. I promise this is worthy of the hype I am giving it.
For our deep dive, we get into the weeds on product positioning. Positioning is one of those topics that does not get all the headlines but can be the difference between a product succeeding or a product failing. Amber walks through an example of an insurance product that was underperforming and how she used positioning to get that product back on track. She breaks down where she started her process for repositioning the product, and most importantly, she gives the results. My favorite part of the results is that product sales went up without having to overhaul the product itself. So often you hear about positioning, but then you look at the product and the product is totally different. In this one, she walks us through how they did not overhaul the product. It is fantastic. So with that, let us jump in and hear how she did it.
Callan Harrington 02:34
Amber, welcome to the show. For those that do not know you in the industry, Amber is the Director of Product and Lifecycle Marketing at Cowbell, and I have had the good fortune to work directly with Amber in the past. Amber, thanks for coming on today.
Amber Wuollet 02:50
Yeah, thanks for having me on. I am excited to chat. It has been a while.
Callan Harrington 02:53
Here is where I want to start. This is going to be an abrasive first question. Tell me about the biggest fail of your career.
Amber Wuollet 03:03
First of all, I love the transparency and diving right in. I am excited to relive my trauma with your audience.
Callan Harrington 03:10
Exactly. That is what we do here on the show.
Amber Wuollet 03:14
I have a fail so epic it still haunts my nightmares. Let us set the scene. Late stage startup looking for that big, go big or go home moment. We decided to go as big as one can possibly go and do an airport installation so large that you could practically see it from space. We were taking over a hallway in a prime spot where high target clients routinely flew in and out. Not just the huge hallway but placements throughout the airport. The hallway was about 15 feet wide, 20 feet tall, and 60 feet long. You had to go through it to get to the main gates.
We built an entire campaign and brand image around this. We created a universe that everyone had to walk through. We had an installation at the beginning of the tunnel and at the end of the tunnel and complementary messaging throughout the airport. We were excited. We had never gone this big before. This was our moment. Local press was excited. Industry publications were excited. I had lined up a live press conference with local news stations. The timing was perfect, right before the big conference season. We would launch this, tease it, have a big news launch, and then everyone would experience it live as conference season rolled out.
We found the perfect date to launch, March 11, 2020, the day COVID shut down the world. The day started out normal. We had heard about coronavirus. It was on our radar, but we had no idea what was about to happen. A crew of us flew to the airport and we were filming. I was waiting for the newscaster. The news station and I had been texting to coordinate. We wrapped the footage we needed to shoot. I will never forget sitting there waiting for the confirmation of when I would go on the news. I was watching the news and getting concerned, but I was so focused on this initiative. The news station called and said they would not be covering our installation. The only thing they would be talking about was the coronavirus. They told me if I were you, I would get home as soon as possible. Hop on the next flight. You do not understand what is about to go down. You need to get home.
That is when it sunk in that six to nine months of planning was circling the drain, and the future of event marketing was about to shut down. I took their advice, got on the next plane home, and tried to figure out what was next. Like everyone else in March 2020, we went into survival mode. What do we do now? What does our events strategy look like now? What does our content strategy look like now? We pivoted. We used the onsite content we had filmed. We shared that. We kept the campaign going and made it a multi touch direct mail focus. We pivoted to virtual events. We created a video interview series. We did the best we could with it.
A Seth Godin blog I read yesterday hit home. Do not judge your decisions only by the outcome. Sometimes good decisions have bad outcomes. A bad decision is one made without the correct context. In Q2 and Q3 2019, we made decisions based on the information available at the time. I struggled with the takeaway, how to never do this again, but the reality is you cannot control the entire environment. I stand by the creative direction and the work the teams did. It did not pan out. We renegotiated contracts and made what we could of it, but sometimes good decisions lead to bad outcomes.
Callan Harrington 08:20
We worked together for that. We had tested airport marketing. It was a bold move to start, and it was strategic. A lot of our strategy hinged on getting carriers in that area. It was not make or break, but if we got them it would be a huge catalyst. Nobody was thinking outside the box like that. Half the company thought it was out there. I thought it was interesting and that it would get attention.
Amber Wuollet 09:07
It was account based marketing on steroids.
Callan Harrington 09:10
Unlike anything I had seen. I use that story all the time. It has the best punchline.
Amber Wuollet 09:19
Brutal. The strategy was solid, the creative was amazing, the team was amazing. Everything was amazing except the date it launched.
Callan Harrington 09:32
There is no world where you can time that. Impossible. I am happy you shared that story. It is one of my favorites. I want to talk about your early career before we dive into the campaign. A pivotal early experience was at AmericInn, a hotel chain in the Midwest owned by Wyndham. How did you get that job?
Amber Wuollet 10:15
I do not think I have told this story on a podcast. We are going into the vault. Very pre internet. I was counting the days until I could turn 14 because I wanted to work. I grew up in a tourist town with many hotels and an amusement park. Some would hire at 14. The week before my birthday, I called places to see who would talk to me so I could start a job the day I turned 14. The first hotel in the Yellow Pages was AmericInn. I called and said I was looking for a job, hardworking, a good student with extracurriculars and references. Could I come get an application? They asked how old I was. I said 13, but I would be 14 in six days. I picked up an application and set an interview for my 14th birthday and got the job.
Callan Harrington 11:36
I dug that one up. It shows a theme of ambition in your career. My first job was at 15 and I did not have that ambition. Now to American Family Insurance. You spent 10 years there in underwriting. How did that impact you when you moved into marketing and how did time at a big carrier impact your career?
Amber Wuollet 12:28
So much. I am grateful I landed where I did for my first insurance role. It was somewhat by accident. My sister, now in legal, had an internship at American Family. After college, I traveled, worked abroad, came back, wanted a real job, and my sister suggested American Family. I saw an opening in the Star Tribune and went for it. Underwriting lets you see everything. I talked to agents, insureds, and claims. I worked on product and marketing projects like launching new discounts and rating structures. I helped launch high value underwriting and wildfire underwriting. I saw so much of the insurance value chain. It shaped my view on marketing, how I talk about insurance in product marketing, how I look at launches, positioning, and messaging. I am passionate about policies and rating programs. I have been in insurance for almost 20 years. I had amazing mentors who explained coverage impacts. We used old green screen mainframes. I looked at application information for home, auto, umbrella. I learned end to end, saw coverage, claims, new business reporting, data and analytics. I am grateful for that and it continues to influence me.
Callan Harrington 14:45
Did it give you better empathy for customers when you moved to insurtech?
Amber Wuollet 15:19
Absolutely, especially having worked closely with brokers. I worked with agents all day every day for 10 years. I am still connected with many of them. I was in the trenches with them. Lines and agencies differ, but challenges have commonalities. Exposure to their world helps. I also rotated into the phone unit and spoke to angry insureds. Why did my policy change? Explaining things like using credit in rating and what happens after a claim. I communicated with insureds and brokers regularly. It helps me craft positioning and messaging and then validate it. I never assume I know what they think. I have educated assumptions and then validate.
Callan Harrington 16:42
How was the transition from a large company to earlier stage companies like EIS and Bold Penguin?
Amber Wuollet 17:04
Strange. At large carriers you have layers, process, robust project management, and a slower pace by design. Then I was working directly with the CEO, CMO, and product leaders and able to pivot quickly. It was uncomfortable at first. Should seven other people review this? Do we need legal and compliance? I learned to be comfortable moving quickly. I was fortunate to have leadership that empowered and guided me. Having both experiences is valuable. I could bring helpful structure to less structured orgs without adding unnecessary process. Finding the balance is a moving target, but I value having had large, small, and medium experiences.
Callan Harrington 18:33
What keeps you in the startup world now?
Amber Wuollet 18:42
I love the stress and chaos of startup life. My sister in government asks why I make my life hard. It is fun. I love the faster pace and intensity. I love working with founders and energized colleagues. I remember launches where we would brainstorm and get excited. That energy is hard to replicate at larger orgs. The impact of your work is visible quickly. You pull a lever and see results in a week. It is fun.
Callan Harrington 20:02
The feedback loop is almost instant. I want to dive into your role today, but first the campaign. We will dive into a relaunch of a product. What led up to it? Why was it necessary?
Amber Wuollet 20:47
I was leading product marketing at a niche liability carrier. A three year old policy was underperforming. I appreciated the appetite to dig in instead of treating symptoms. Sometimes we lower price or make a new sell sheet. Sometimes that is part of it, but I was given authority to dig in. Three years in, it is not selling. We are a fraction of where we want to be. Let us dive in. This was an ideal scenario to run end to end go to market for an existing product in a fresh way.
We started with internal voice of business research. Talk to distribution and underwriting. What did they think? What are they hearing? How did they feel about the original launch? I was not there for the original launch. What worked and did not work. Then external stakeholders. We did 45 minute recorded one on one interviews with about 15 brokers and 15 clients. This was a three to four month process to conduct and analyze interviews. We made it qualitative and quantitative. We added simple NPS style questions so I could present metrics along with quotes. How likely are you to quote this product in the next six months? In the next three months? What if this?
Findings. Price comes up. It always does. But other things came up. We had positioned the product as new and advanced with lots of value and features. We tried to communicate value, but we communicated complexity. Newness was not seen as positive by many. A few clients said they did not want to be a guinea pig and to come back when it was ready. We inadvertently communicated it was untested, which was not true. It was approved and not far off from things we had done.
We reworked positioning and messaging. We backed off newness, complexity, and the acronym. We framed it as protection for high verdicts. Call it verdict protection in conversation. Simplify it so it is easier for brokers to sell and policyholders to buy. Invest in messaging by audience. For brokers, make it easy to sell and to add into conversation. For policyholders, be clear about value. We adjusted pricing and processes and set goals. Align on what you want to achieve and how you will measure it. How much do we need to sell for success. Align so you can iterate. We aligned on a goal, implemented new messaging and positioning, and built new assets like PowerPoint slides, a style sheet, and a teaser video. We blew the goal out of the water. We had a 12 month goal and hit it in six months. It was incredibly collaborative. It cannot be product marketing alone. It needs underwriting and distribution aligned. Product marketing organizes, but everyone works together. Simplify, create new assets and messaging, and ensure it is customer driven.
Callan Harrington 26:18
You did internal interviews and external interviews, rebuilt brand positioning and key messages for agents, partners, and others, then did a full relaunch and built all the assets. Am I tracking exactly?
Amber Wuollet 27:08
Yes. The question sets were very different. We used internal feedback to draft the external question set. Phase one and phase two. We talked to small internal groups first and kept it off the record. Tell it like it is. If marketing gave you a terrible sell sheet and it did not work, say so. With brokers, we asked what did not work, what would incentivize you, and what value you see. With clients, who is this for and who would it appeal to. That is a huge part of positioning. Figure out who. You have an ideal customer profile, and others outside of ICP can purchase, but you focus on that first. Maybe this is not for everyone. Maybe it is for large health systems. Then adjust creative and messaging accordingly. It is a waterfall approach using internal feedback to craft external stakeholder feedback.
Callan Harrington 28:34
Did you record internal interviews or avoid recording to get openness?
Amber Wuollet 28:41
I wanted to record for accuracy but worried it would incentivize people to hold the party line or avoid saying negative things. I made groups small and did not record to encourage transparency.
Callan Harrington 29:07
How many interviews did you do total and how did you set targets?
Amber Wuollet 29:56
About 33 to 35 total including internal. I wanted all key segments represented. At least two to three small, medium, and large. Two to three from different geographies. Specialists in the liability we sold and generalists. On the client side, small, medium, large, and all geographies. I hypothesized differences by state based on legislation. Some states have jury verdict limitations where you might not need this as much. That set the bare minimum of about 12 to 15 to cover voices. We were fortunate to leverage existing broker and client advisory councils and then supplement.
Callan Harrington 31:24
One of the big insights was that for the segment writing the policy, messaging and positioning were off.
Amber Wuollet 31:41
Yes. Understand what is important. They were looking for tried, true, and tested. Easy to buy, easy to explain, familiar, and trustworthy.
Callan Harrington 32:03
What did the actual launch look like?
Amber Wuollet 32:23
I use four quadrants for launches. On one end, low hanging fruit like a newsletter inclusion. On the other, multi event strategy with digital ads, out of home, and strong PR. Lots in the middle. Goals matter. We set a sales goal. What needs to be true for that goal. Do we need a press release or reinsurance media. In this case, no. It was hyper niche. We needed about 20 percent of broker partners on board and excited. That is a small number in a niche world. The launch was strategic but right sized. We built a new set of sales enablement tools including several videos, but we focused on the specific audiences through existing channels. No billboards, no press release, no broad media.
Callan Harrington 34:21
Did the product change?
Amber Wuollet 34:35
No. Positioning and messaging changed. No refiling or policy document changes.
Callan Harrington 34:48
How gratifying was that?
Amber Wuollet 34:52
Very. It was good for insureds and for us. It shifted limit structures to where coverage is needed for jury verdicts. Better for risk structure and the industry.
Callan Harrington 35:39
Often marketing is asked for leads and new business, and it is hard to put hard ROI on brand and positioning. This is a perfect example since the product did not change.
Amber Wuollet 36:17
Yes, and goals are important. Leadership was excited about limits shifting to the verdict protection piece as well as sales. Understand what is important to internal stakeholders and share success in their terms. I am excited about open rates and NPS, while general counsel and the chief underwriting officer care about other metrics. Think through that lens so everyone sees the success.
Callan Harrington 37:10
After launch, when you spoke with brokers responsible for most of the business, did the new messaging click right away?
Amber Wuollet 37:32
Yes. Even brokers who had never sold it before were candid that it looked complicated and would add time to every new business call. I appreciated that transparency. Once I explained it simply, they saw the value. We also repositioned pricing as a percentage less than standard excess to make the value clear. Underwriting got excited too. We talked about it in all hands. I joined underwriting calls. I sent weekly updates on progress to goal to keep momentum, calling out milestones and wins.
Callan Harrington 38:51
Let us talk definitions. What is product marketing to you?
Amber Wuollet 39:36
Product builds the product. Product marketing gets it on the right shelf and off the shelf. It is the business end of marketing. The line between product marketing and marketing varies and requires communication. I draft positioning and messaging with SMEs, then hand off to copy and design. Sometimes I draft parts of the sell sheet copy. Then who writes the email, me or content. If you do not have a product marketer, someone is doing product marketing.
Callan Harrington 41:13
Will AI supercharge product marketers?
Amber Wuollet 42:36
It helps, especially research and synthesis. Validate sources to avoid hallucinations. Sometimes validation takes longer than searching directly. I still use AI daily for first passes and to make sense of stream of consciousness notes. It expedites product marketing work.
Callan Harrington 44:09
Define lifecycle marketing.
Amber Wuollet 44:58
Lifecycle means the work does not stop at launch. It includes onboarding, nurture, engagement, and retention. Onboarding is critical. Voice of business and voice of customer inform cadence and content. In the first 90 days, what questions do we get, what are complaints, what do we wish they knew, and what behaviors do we want to incentivize like early reporting. Watch data in real time for opens, clicks, and unsubscribes.
Callan Harrington 48:00
If you could talk to your younger self, what would you say?
Amber Wuollet 48:12
Keep going. It pays off. I had a quarter life crisis, felt behind, did not have the best degree, and was not keeping up with my vision. I kept showing up. Careers are not linear. They are wiggly. If you are lucky, the trend is up with setbacks along the way. Comparison is the thief of joy. Keep plugging away and you will be happy where you land.
Callan Harrington 49:08
Comparison is a constant struggle. I have gotten better but it is hard. There is always someone doing better. Always. And there is probably something else not going well that we do not see. Amber, this was so much fun. Thank you for coming on today.
Amber Wuollet 49:35
Thanks for having me.
Callan Harrington 49:44
I hope you enjoyed my conversation with Amber. I loved talking about positioning. If you want to learn more about Amber, you can find her on LinkedIn in the show notes. If you liked this episode, you can find me on LinkedIn too. Let me know. If you want to support the show, give us a follow on YouTube or leave a review on Apple Podcasts or Spotify. Thanks for listening and I will see you next week.