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Leadership Edge with Avalara’s Jay Lee

Jay Lee oversees Avalara’s growth in business through marketing, product development, and business strategy. He brings more than 20 years of experience developing high-performing marketing teams that are empowered to increase customer engagement and drive financial results. Prior to Avalara, Jay served as the global head of marketing for PayPal’s Business Financing Solutions division, where he helped small businesses obtain financing to achieve their aspirational goals. He has previously held leadership positions at large companies like American Express and GE, as well as smaller entrepreneurial companies like Aimia and Swift Financial.

Thank you so much for doing this with us! Before we dig in, or readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

I actually started my career as a systems engineer working in the technology department of an investment bank. Back then, it was the early days of large databases, integrated systems, and productivity through automation. My role involved managing system uptime, performance, and capacity planning. Eventually, as I was working on developing a technology-based product I found myself taking on more of a product manager role informing the entire go-to-market strategy. It was at this moment that I began transitioning into a more formal marketing role and found myself loving the customer centricity of marketing. In framing the messaging and go-to-market strategy, I had the opportunity to truly put myself in the shoes of the customer and ask, “what’s in it for me?”

Can you share a story about the funniest marketing mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I only have one funny marketing story and it relates to direct mail — a marketing channel near and dear to my heart. Early in my career, we had put out a significant amount of direct mail only to find that the toll-free number we had listed on the materials was wrong. It was the time where alternative “800” numbers where being introduced to keep up with demand. We quickly learned a hard lesson from this mistake as the incorrect number directed callers to an in-appropriate hotline! We tried our best to purchase the phone number from the other organization but were unsuccessful and had to deal with the fallout. Note to self — the editing process is key!

Are you able to identify a “tipping point” in your career when you started to see success? Did you start doing anything different? Are there takeaways or lessons that others can learn from that?

Given my engineering and technical background, data has always been at the core of what I do. Because of this, I guess the “tipping point” in my marketing career happened when marketing started to become much more analytical and data centric. The ability to track, measure, test and learn in marketing was the big game changer on the road to producing repeatable and ever improving results. More recently, the ability to improve targeting, leverage models and prediction, customize customer experiences, and quickly test and learn is creating the next step up in marketing. The big difference now, is leveraging technology to make your message have greater impact to the right audience.

Obviously, this analytical shift in marketing really accelerated with the rapid evolution of digital marketing. In the early days, good marketing revolved around the lists that you could buy. Digital marketing started as a scale play, but quickly evolved to relevance in the buyer journey. Now, marketing is all about leveraging the insights gained from as many data sources as possible to heighten that relevance. As I look back on my career, the shift to analytical and digital based marketing solidified my career in marketing.

What do you think makes your company stand out? Can you share a story?

Avalara is truly one of those “pioneer” companies. Avalara helps businesses understand and manage their tax compliance obligations, a task that no business could have imagined would become so burdensome and complex. While the concept of tax is something that has been around since the dawn of humanity, when Avalara was created 16 years ago the company envisioned a world where technology would store all the crazy rules that the government dreams up and “automagically” pump out the answers to every permutation that is created in commerce. This vision, now real, completely disrupted the status quo — simplifying inaccuracies and reducing complexity. Avalara has leveraged SaaS and automation to create an entirely new category within the regulatory tech industry.

Perhaps one of the best stories is seeing this vision really validated with the Wayfair legislation, underscoring the need for an end-to-end full suite compliance platform for all businesses. Avalara went public literally six days prior to the ruling and had the solution to the problem that the new legislation would create.

There have been innovations taking place across all sectors of business via SaaS for years. However, the use of SaaS in the compliance world is just getting started. I think Avalara has the opportunity to help shape the way that this industry and our government’s thinking around sales tax evolves. From a marketing perspective the opportunity to shape and drive the narrative for the entire industry is extremely exciting.

Are you working on any exciting new projects now? How do you think that will help people?

I am relatively new to Avalara and I’ve joined at an exciting time. We are transitioning from being a private company of nearly 16 years to operating as a publicly traded, global company. As such, we’re transforming our marketing organization to take us to the next level.

At this stage of our company lifecycle, the goal is to scale efficiently and help as many businesses manage an incredibly painful sales tax management problem. The real competition is the manual approach business perform when there is an easier, more cost-effective way to handle it. I get energized when I get to work with people who are passionate about helping small businesses succeed. The marketing organization is certainly eager to help Avalara become the de-facto solution in the industry.

What advice would you give to other marketers to thrive and avoid burnout?

  1. Make sure that you love what you do — You should have a passion for what you’re doing and ensure that you have a clear image of the impact you want to make.

  2. Enable your people and teams — My top priority as the CMO is to organize our team for maximum effectiveness. Like any great team, it works best when everyone gets to play to their strengths. Given the growth we think we can achieve, having the team operate in their power zones is job 1.

  3. In marketing, failure truly is learning — One of the best things about marketing is that you have the opportunity to test and learn. At the end of the day, there is no wrong answer in marketing. If your campaign flops, you can learn from it. Marketing is like a puzzle that you get to constantly keep solving don’t get discouraged if things don’t work.

  4. Surround yourself with the right people — Just as important as enabling your teams is making sure you have the right team. No one is an expert at everything, so having the right mix of super-powered team members is key to making it all fun.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Everyone has the one person who was willing to take you under their wing and teach you the ropes — a teacher, a coach, maybe an older sibling. For me, it was a consultant to the company where I started my first job out of college and quite ironic. My leader did not have time for me, but someone who was not even an employee was willing to give of himself and ensure that I was always pointed in the right direction. It’s a special and generous character trait to want to impart knowledge and wisdom on others rather than just be self-centered. I think that everyone should think about what they are truly gifted at and try and teach that to as many people as possible.

Ok super. Let’s now shift to the main part of our discussion. There are hundreds of memorable marketing campaigns that have become part of the lexicon of our culture. What is your favorite marketing or branding campaign from history? Can you explain why you like that so much?

There are so many excellent campaigns that have made their impression over the years. The one that stands the test of time for me is the “Mean” Joe Green Coca-Cola classic ad. It’s emotional and heartfelt and had a very simple message that sharing a Coke could bring people together. I think that I liked it so much because no matter how many times I watched it; I could not help but smile.

If you could break down a very successful campaign into a “blueprint”, what would that blueprint look like? Please share some stories or examples of your ideas.

There are all different kinds of campaigns that exist from brand awareness to direct conversion, but I would say that the standard blueprint stays relatively the same:

  1. Define your objectives and goals for the campaign.

  2. Understand the ideal customer, and the problem you are trying to solve for them in the way that the customer experiences it and describes it.

  3. Identify where they place mindshare and target them in those channels as close to moment that your solution is most relevant

  4. Messaging your value prop clearly, in a way that states the outcomes that the customer would like to achieve

  5. People make decisions emotionally — so try to make your campaign emotionally relevant.

An example I know well is marketing business loans to small business customers. You should have an ROI calculated for the campaign which is governed by expected response and loan booking pull through. You can use all forms of data to hone in on the prospects that are both likely to be approved and in the segment that could borrow the average size you are looking for. Ideally, you have triggers in data that allow you to know when they are in the market for a loan. You should time your campaign across those channels where they are most likely in the mindset to be receptive.

Companies like Google and Facebook have totally disrupted how companies market over the past 15 years. At the same time, consumers have become more jaded and resistant to anything “salesy”. In your industry, where do you see the future of marketing going?

Consumers increasingly know that we now live in the attention economy. Perhaps worse, it is possible to outright spread falsehoods and fake news with little to no repercussions. Luckily, consumers are getting wiser about how the attention economy has really driven news and content on the web and are now taking everything with a grain of salt.

The future of marketing really goes all the way back to the authenticity of the mission and visions of companies. No great marketing campaign is going to be able to fool people to inauthentic products or causes. Companies must have a genuine purpose and live by an authentic brand with aligned observable values. Consumers today are looking for more in the products and services they use and in a real way are more and more voting with their dollars. Great marketing begins with great products and services and done well, it really brings out that core message in a way that is authentic and resonates.

Can you please tell us the 5 things you wish someone told you before you started? Can you please share a story or example for each?

Be humble

  • The most effective people are those that everyone can relate to and create a rapport with. However, I think that we all start our careers off trying to stand out amongst peers. All children are taught this at an early age as they try to get into colleges and universities. But in the real world, successful people are those that create effective harmony and try and bring out the best in others.

Listen more

  • How many great ideas in marketing weren’t yours? In fact, there really are no good or bad ideas — there are ideas that work or don’t work in the market. My first lesson in this was this ugly direct mail package which came from this very reputable agency. I swore that I would not spend money mailing it. But I came around, and lo and behold, it blew the doors off our control.

Play to your strengths (and let others make up your weaknesses)

  • So much of our upbringing is about trying to be great at everything. But, when we look at teams, it’s about having really talented people in the right positions. Make sure that you are better than everyone else at one thing and find the right role that lets you exploit it. Don’t waste time trying to fix your weak areas if you have not figured out what you are truly great at first.

Measure and track it

  • It’s the bane of every marketer’s existence — channel attribution. In today’s marketing you must continuously improve your tracking and attribution model. It will never be perfect, so you need to know where you have inherent biases and take them into account to make the right decisions.

Speed, speed, speed

  • There is a great quote from Peter Senge that I heard early in my career but did not realize the importance until later. “The only sustainable competitive advantage is an organization’s ability to learn faster than the competition.” Nowhere is marketing’s speed to insight more needed than in an industry with disruptive SaaS companies emerging. The faster you learn about your customers and testing into marketing strategies to find what works, the faster you separate yourselves from the competition.

Can you share a few examples of marketing tools or marketing technology that you think can dramatically empower small business owners to become more effective marketers?

Today’s SaaS services have dramatically leveled the playing field between smaller businesses and the larger ones. With a little investment in time and practice, you can create a business that is as engaging and professional looking as any $100M revenue company. Some of the marketing tools that I believe can empower small business owners include:

  • Website E-Commerce software or WordPress — There is no reason that any small business needs to toil through the development of an awesome looking website anymore. There are so many easy to use services that allow you to make your own online site.

  • Email Software — Email software companies are so robust you can get excellent customer relationship management (CRM) capabilities that are easy to integrate with your website for new customers and emails to loyal ones.

  • Facebook and Google Advertising — If you have marketing dollars to spend and have covered all the bases on owning your own listings — then the starting points are Google and Facebook. Their built-in tools are easy enough for the beginning to create campaigns across their properties.

  • — Since we are not all gifted at being great designers, Envato is my top recommendation for a business to go and leverage pre-built templates and digital assets for literally any type of marketing you want to create.

The barriers to getting a business off the ground are low, but the barriers to success remain high. While the tools exist today to help small business owners improve their marketing efforts, there is still an inherent need to understand how to effectively reach your target market because fewer ecosystems are controlling the access to larger numbers of customers.

What books, podcasts, documentaries or other resources do you use to sharpen your marketing skills?

I don’t follow a lot of marketing blogs or have any specific books I would recommend; however, I really enjoy entrepreneurship books and I highly recommend Hidden Brain podcast hosted by Shankar Vedantam from NPR. It is a great podcast on human behavior and always gives incredible insights into how people think and make decisions.

Who is your hero? Can you explain or share a story about why that person resonates with you?

My personal hero is Roger Federer. To me, he is the greatest tennis player of all time. He’s defined perfection in the game, has endured over so many years, is a true sportsman, a master tactician, a hard worker, a generous and giving individual, and has stayed authentic to his true self as demonstrated through his love of the game. Wherever he plays around the world, he has the home court advantage.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

If there were a way to end prejudices, that would be the movement I wish I could inspire. So much good would come if people could understand and truly relate to one another. I think that we would find that we are all not really that different.

How can our readers follow you online?

Thank you so much for joining us. This was very inspirational.

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