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Authority Magazine: Ashley Flood of We Are Rosie On Five Things You Need To Be A Highly Effective CRO

by | May 22, 2023

Ashley Flood, We Are Rosie's CRO

Originally posted on Authority Magazine on May 19, 2023.




An Interview With Rachel Kline

Strategic thinker and operational leader. Strong leadership skills. Customer centric. Great decision maker. Take risks and embrace failure.

ACRO’s role is essential for a company’s growth, taking on the responsibility for all aspects of driving revenue to the company. What makes someone an effective CRO? For someone considering a role as a CRO, what does it take to create a highly successful career in this position? To address these questions, we had the pleasure of interviewing Ashley Flood.

Ashley Flood is Chief Revenue Officer at We Are Rosie. In her role, Flood is responsible for driving growth by developing strategies to maximize revenue and leading the company’s sales and client operations teams. Flood joined We Are Rosie with 20 years of experience in strategic planning, digital media and advertising sales. She spent nine years at Twitter where she helped establish the company’s CPG business and led a team focused on growing revenue and strategic partnerships with Fortune 500 companies. Before that, Flood held roles at Google, the American Red Cross and Starcom Worldwide.

Thank you so much for your time! I know that you are a very busy person. Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Career paths are often not linear and mine certainly isn’t. As a child, I had my heart set on going into broadcast journalism. I grew up on a farm, in a small town in Kentucky, and had dreams of settling in the Big Apple and working for one of the large broadcast networks. I got the opportunity to test out those dreams one semester of college as a production intern at the Today Show in New York City. The experience was amazing but ultimately, after college, I decided to shift gears last minute and took a job as a media buyer and planner in Chicago. Little did I know where that would lead me. In that role, I became fascinated with using strategy, insights and planning to drive business outcomes for clients. I stumbled into a role at Google (before any of us really knew how to Google) where I was fortunate to partner with the world’s largest brands to disrupt and digitize their marketing models. I like to think of my experience at Google as getting my MBA in sales and marketing. It sharpened my sales IQ, challenged me to think like an entrepreneur, taught me how to be both a business and people leader and essentially teed me up for my next few roles at Twitter, where I helped to establish and grow the company’s business with CPG companies.

During my time at Twitter, I was given the opportunity to work remotely which enabled me to be closer to my support network and honor the life I wanted to live without sacrificing my career aspirations. I am the beneficiary of flexible work and see first-hand how it can help an individual bloom and organizations thrive. And that is why I was so drawn to We Are Rosie and our mission. We are an inclusive, flexible work marketplace that exists to enable people to live the life they deserve and still have the careers they want. There were so many times in my career where, as a mom, I really questioned ‘Can I do both? Can I be a mom and be successful at work? Can I be the CEO of my household and still break the glass ceiling?’ We Are Rosie is making that possible for thousands of caregivers, people of color, members of the LGBTQ community, veterans and others who desire and need a better way to work.

It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you first started? Can you tell us what lesson you learned from that?

Oh geez. I’ve made more mistakes than I can probably count and I don’t know that any of them are funny, even now. There’s one in particular that was more humiliating than anything but certainly taught me a lesson. When I was new in my role as a Media Associate, I remember a time when I thought I was emailing a peer but emailed a vendor instead with information that was meant for internal eyes only. It certainly wasn’t the end of the world but a careless mistake that taught me to slow down, always proofread my work and how to take accountability for my mistakes.

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

This one is easy for me. Aside from my parents who made me believe that anything is possible, my greatest teacher in business is Matt Derella. Matt was one of my bosses at Google and he took a chance on me. At the time my ‘pedigree’ didn’t map back to the open role on his team but the potential was more than there. Matt saw that potential and was able to push through the red tape to hire me onto his team. Matt was always good about spotting my imposter syndrome a mile away and he constantly pushed me beyond my comfort zone to help me realize my full potential. Beyond that, he was a master at giving feedback and the person who taught me “feedback is a gift.” I’ll never forget a meeting he and I had with our VP of Sales at the time. Despite rigorous prep, my nerves got the best of me and I completely bombed it. Matt knew I was my own worst critic so he kept his feedback to a minimum but said ‘that wasn’t your best meeting.’ He was more than right. I hate to fail and let people down and so I promised myself I would never let that happen again. To this day, I have a little routine I follow to get my nerves in check before a meeting and you can bet I never show up unprepared.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  • Growth Mindset — For as long as I can remember I have loved a good challenge, so throughout my career I have run towards challenges while others were running away. Because of this, I pushed boundaries and came to realize my true potential which then gave me the confidence to pursue roles and opportunities I may not have otherwise. I believe a growth mindset is also a catalyst for perspective, and perspective is so important to being a successful leader. Being able to bring perspective to the table, especially amidst challenging circumstances, can help ground and motivate teams to persevere and achieve their goals and the company’s goals.
  • Accountable — I always set the bar high for myself when it comes to accountability and I expect the same from my team. Accountability to me means I never let more than 24 hours pass before following up with a client, meeting every deadline or managing expectations if I’m going to miss, following through on my action items after a 1:1 or holding myself accountable when I get it wrong, which I often do. Accountability builds trust and is the difference between good and great. I’ve found there are a lot of good leaders out there who can talk the talk but it’s the ones who can walk the walk that see the most success. I always strive to be the leader who walks the walk.
  • Empathy — I have always gone out of my way to show I care and really get to know my peers, clients and team members on a personal level. This has enabled me to build deep, trusted relationships and a strong network which has opened doors and opportunities for me over the course of my career. I have found as you advance in your career, who you know becomes just as important as what you know. The network I built by showing empathy to everyone whose path I crossed undoubtedly landed me the role I am in today.

Thank you for all that. Let’s now turn to the main focus of our discussion about creating a successful career as a CRO. For the benefit of our readers, can you help explain what exactly a CRO does? How is a CRO different than a CMO or a CFO?

As Chief Revenue Officer, I’m responsible for growing our business by defining how we go to market and identifying new strategies and products that maximize revenue. I am constantly thinking about ways we can provide innovative marketing solutions to our clients to help them solve their biggest challenges and partner very closely with the CFO and CMO.

The CMO is responsible for our brand, clearly defining who we are, why we matter and how we show up and packaging this into a toolkit my team can take to market. As for the CFO, revenue is just one piece of their job. They are responsible for forecasting, the steward of all of the company’s assets, responsible for cash flow, analyzing opportunities and weaknesses to inform our action plan and, more and more, looking ahead at trends and opportunities to future proof our business.

Can you tell us about a project, person, or a team you led where you successfully made a big impact? What secrets can you share with us?

In my role as Senior Manager at Twitter, I was fortunate to build a team of high performing individuals who grew to be among the best talent in the company and drove outsized results for the business. Looking back on it there were four things I got right that enabled this dream team. First, from day one I focused on empowering them vs managing them. This is not to say I didn’t ever have to ‘manage,’ but starting from a place of empowerment built trust and enabled me to achieve their buy-in over time. Second, I approached hiring as a casting agent vs a hiring manager. I wasn’t simply trying to fill an open head. Instead, I saw it as an opportunity to cast an individual who would align perfectly to that specific business and client, while also augmenting the team by bringing new expertise or a skill that was previously lacking. Third, I placed a heavy emphasis on personal development and invested a lot of time with each individual to ensure they had a development plan, as well as did my part to support that plan. This led to high engagement levels, increased morale and strong performance. Finally, I created a psychologically safe space where everyone had a voice, every perspective was welcome and feedback was seen as a gift.

Have you ever been presented with a difficult situation that required creative problem-solving? Can you please share the story with us?

When I think of difficult situations, my mind goes back to the spring of 2020 when the world started to shut down due to the global pandemic. Everything about that time was difficult. Our clients were pausing all advertising spend, we were forced to rethink how we worked overnight and our personal lives were being disrupted left and right . There was certainly not a playbook for this and it really tested me on both a personal and professional level. How was I going to keep a team of salespeople motivated and engaged? How would we achieve our revenue goals if all of our clients were paused? The first step was to acknowledge how difficult this was for everyone and reset expectations based on what was in our control at that time. As it related to the team, we found new ways to build connections in a time of isolation. We started virtual book clubs, had virtual bake-offs, sweated through virtual workouts, hosted weekly Breakfast Clubs with a new team member leading each week and led gratitude circles. Through each of these we saw our co-workers through a deeper lens, which formed a bond that became impenetrable.

On the client side, we had to re-allocate resources accordingly, find new ways to add value to clients and re-imagine campaigns in order to meet people where they were — in their homes. It unleashed a new level of creativity we may have not seen otherwise. For example, Gatorade was one of my clients at the time and with sports postponed indefinitely, no athletes on the court, no spectators in the stands and no viewers at home, the brand had to re-imagine their marketing plans. Knowing Twitter was always the roar of the crowd and the home for real-time sports, Gatorade turned to us and we, in partnership with the NBA, were able to create a watch party experience and live stream Game 6 of the 1998 NBA finals. The program gave Gatorade’s athletes and NBA fans the chance to relive the fun and excitement of the Chicago Bulls final title run and the brand the opportunity to connect with their athletes in a compelling way. It was a win-win for both the brand and the rest of the world as we craved normalcy and connection.

Here is the primary question of our discussion. Based on your experience and success, what are your “Five Things You Need To Be A Highly Effective CRO?” Please share a story or an example for each.

  1. Strategic thinker and operational leader — To be effective you need to not only be able to think big but you also have to be able to land the plane. Strategy is useless without tight execution and the how is just as important as the what. An example that comes to mind as I think about this is how I approach business planning. Annual business planning is a three-step process that doesn’t just happen once a year. It starts by setting the strategy and the key priorities we will focus on throughout the year. Once we have alignment, we immediately switch to project management mode and map out all the activities we need to do, by quarter, to hit our goals and then establish quarterly check-ins to track progress and drive accountability.

2 . Strong leadership skills — As CRO, you aren’t just a business leader. You also have to be a great people leader because your people are your strongest asset. Even the best product doesn’t sell itself. A CRO needs to be great at casting talent and teams and then continuously finding ways to inspire, motivate and guide the team to greatness. When building a new team, I like to spend time getting to know each individual on a deeper level. I lead GROW sessions with every member of my team to learn more about who they are, where they are from and their aspirations. These sessions have been invaluable in uncovering their values and motivations which has enabled me to speak their ‘love’ language, increase engagement and build teams of high performers that drive strong business outcomes.

3 . Customer centric — The CRO needs to have a deep understanding of their customers so they can develop trusted relationships and become the counsel they seek out to help solve their biggest problems and challenges. At We Are Rosie, we have two customers — our community of 25,000 marketers and our clients. When I first joined the company and started in this role, my first order of business was to meet our clients and our Rosies to ensure that every decision from that point forward, every process we implement and product we bring to market have these two constituencies in mind.

4 . Great decision maker — As the business leader, people look to you to make the call and you have to be comfortable making decisions. I tend to be the person who likes to have all the facts and noodle a decision to death. Unfortunately I don’t have that luxury in this role. There isn’t a day that goes by where I’m not pressed to make a decision on the fly and I’ve had to get really comfortable being uncomfortable and drawing from past experience and my intuition to call a shot.

5 . Take risks and embrace failure. To win big you have to make big bets and take calculated risks. Even the most experienced CRO won’t win them all and that’s okay. Life’s greatest lessons often result from our biggest failures. It’s important to embrace failure, take accountability and learn from any mistakes. I remember a situation a few years ago, where my team had the opportunity to partner with a client to test out a new advertising model. If successful it would mean we could potentially double and even triple our revenue. Music to a CRO’s ears. If it failed, we risked significant exposure and losing the client’s business altogether. In this instance, the reward, as well as the opportunity to learn, far outweighed the risk so we moved forward. And we failed. Ultimately the new model didn’t deliver on its promise and the client pulled their investment. As difficult as it was to lose the revenue, we learned so much about our product gaps that we may never have known otherwise. Yes, a side of the business was exposed but that exposure forced critical updates that would later enhance campaigns and strengthen our client partnerships.

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. 🙂

In 2021, I was diagnosed with Stage 1 Breast Cancer. I found it through a routine self-exam, that honestly, I had probably only done a handful of times in my life. Breast cancer, when caught early, is very treatable so if I could inspire a movement, it would be around self-exams and free preventative health screening for both men and women. We can save hundreds of thousands of lives by being more diligent about self-care and making it affordable for all.

How can our readers further follow your work online?

Feel free to find me on Twitter @ashleyflood or on Linked In:

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