Part of being a leader is teaching people to push their boundaries, both as individuals and in the context of a group dynamic. Early on I gave people the space, time and materials to solve problems believing that an open field was the most fertile ground for creative thinking. I began to see that while people appreciate that latitude, it doesn’t always result in the best outcomes. One day, I read the story of Southwest Airlines and the challenges they encountered early on. Rather than face bankruptcy, the airline had to sell one of its 4 planes, which would force the company to reduce available routes and potentially layoff staff. Instead, the business found a way to be more efficient — drastically reducing gate turnaround time and allowing them to keep all existing routes. Since then, every brainstorm I lead I find a way to make the group’s task slightly more challenging — often by reducing a critical factor like time, budget or another key resource — placing the most obvious path to success out of reach. When I do, I see a level of creativity and problem solving out of individuals and teams that truly astounds me.
I had the pleasure to intervew Dina Chaiffetz. Dina is the Director of Product Strategy at Prolific Interactive, a mobile-focused product agency in Brooklyn, San Francisco, and Durham. As a key member of Prolific’s management team, she leverages her knowledge of consumer behavior and product design to create insightful mobile strategies for leading brands including Gap, Sephora, and Havenly. She also serves on the leadership team of Women in Wireless San Francisco, a networking group for female leaders in the mobile and digital space.
Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?
After college, I spent about 10 years in marketing trying my hand at all the different sub-disciplines to ensure I had a well-rounded perspective. When I was asked to join an early-stage startup as the Marketing Director, I jumped at the opportunity to build a brand and marketing team from scratch.
Because we were a small team, I ended up working on a lot of things outside of the marketing realm, including pitching investors and building the product itself. I fell in love with the process of building digital experiences from scratch.
I also realized that product strategy was the ultimate form of marketing. As I evaluated what feature sets should make the cut in the next release, I could think ahead to what the go-to-market strategy would be and visualize the campaign.
After that experience, I continued to pursue roles where I could leverage my marketing background to truly build experiences with the target market in mind.
Can you share a story about the funniest mistake you made when you were first starting?
One time I sent out a press release on PR Newswire with the CEO’s personal phone number included. What was I thinking? I don’t know. We were a small company and didn’t have a primary office phone number — we all just used mobile phones.
It made sense to me to include contact information in the press release, but I didn’t make the connection that people (and likely bots) comb those sites for sales leads and that he was about to get a ton of unsolicited phone calls.
He was nice about the whole thing, but I felt extremely guilty for weeks!
What do you think makes your company stand out? Can you share a story?
One of the mottos of our company is screw obstacles. Any time we’re presented with a challenge — technical constraint, limited timeline, or a missing resource — we figure out a solution that allows us to build a fantastic mobile experience. Our founders effectively modeled this approach in the early days of the company, embracing any roadblock as an opportunity for innovation.
As an example, one of our teams was working on building an augmented reality experience for the mobile app of a massive home improvement brand called Build.com. Our partner wanted to start with faucets and chandeliers, two popular items sold on the site. The challenge was that the team was using Apple’s development platform for AR (called ARKit) and the platform didn’t support the ability to detect and place an object on the ceiling — making it hard to bring the chandelier experience to life.
The team figured out two ways around this. First, they developed a custom solution to automatically detect the ceiling by using the scanning ability of ARKit to identify points on the ceiling. After testing the experience, they found that the capabilities weren’t ideal for users so they developed a second approach. The team created a guided experience in the app to help users manually identify the floor, and then measure up to the ceiling plane themselves.
Not only did the team solve this problem, but they took the experience a step further. They added the ability to turn on the lights of the chandelier, change the finish and adjust the chain length of the lighting fixture. Their problem-solving and ingenuity led to multiple awards for the experience.
(Check out the experience by downloading the Build App and exploring more than 600 products with In-Home Preview.)
Are you working on any exciting new projects now? How do you think that will help people?
Always! Historically, Prolific provided product teams dedicated to designing and developing premium mobile apps. After years of designing and developing with companies like Saks Fifth Avenue, Scotts and American Express, we’ve come to see the additional needs of organizations around mobile experience such as strategic planning and organizational readiness.
I am working on defining a new class of services at Prolific which will allow us to expand on our current offerings and respond to a shifting market. This will allow us to help companies create clarity and de-risk their investments in mobile by assessing the opportunities and defining a plan of action rooted in clear business outcomes.
This is a new adventure for me. I’ve often been in a position to define a new product experience, but this is the first time I will be defining a new service experience.
What advice would you give to other female leaders about the best way to manage a large team?
As a team grows in size, it needs some form of glue to hold it together over time. That best possible glue for a large team is the organization’s vision and values — more specifically, how a given team or department contributes to the organizational vision and applies organizational values.
Not all team leaders take the time to break down those higher-level components into something tangible at a team or department-specific level. But, that is the necessary step to ensure alignment and cohesion as a team scales. As new members join the team, it ensures there are clear marching orders and a sense of how each new person will uniquely contribute to the success of the organization as a whole.
Plus, as it becomes harder to keep track of the daily or weekly activities of different team members, a strong sense of the team values and vision helps ensure all members are working towards the same goal using a shared cultural code.
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?
One particular person who has helped me professionally in countless ways actually started by getting me in trouble. I met Justin Anthony when he reached out to invite my organization to participate at an event for his nonprofit. GoodSpark was intended to engage and empower the next generation of philanthropists — a mission I was enthusiastic about supporting.
I told him we were interested, but I needed to run it by my board members first. In his excitement, he sent out an email announcement referencing our involvement before I got the green light from the board. Whoops!
Despite the awkward nature of our first encounter, Justin went on to hire me in a freelance capacity and took me under his wing over the next five years. I learned a lot about leadership from him, including how to lead from a place of honesty and integrity.
How have you used your success to bring goodness to the world?
For the last two years, I’ve served on the leadership team for mBolden (formerly Women in Wireless) in San Francisco, a national nonprofit that champions women in leadership in the mobile, digital and tech industries.
As the Content Co-Chair, I work on programming that helps inspire and educate professional women at different stages of their career. One event I am particularly proud of putting together was an all-female VC panel with partners from New Enterprise Associates, Foundation Capital and GGV.
What are your “5 Leadership Lessons I Learned From My Experience” and why. (Please share a story or example for each.)
1. Constraints Are Key for Innovation
2. Transparency and Trust go Hand in Hand
3. “Disagree, But Commit” Doesn’t Always Cut It
4. Rituals Are A Powerful Way to Unite People
5. Imposter Syndrome is Something You Don’t Grow Out Of
Constraints Are Key for Innovation
Part of being a leader is teaching people to push their boundaries, both as individuals and in the context of a group dynamic. Early on I gave people the space, time and materials to solve problems believing that an open field was the most fertile ground for creative thinking. I began to see that while people appreciate that latitude, it doesn’t always result in the best outcomes.
One day, I read the story of Southwest Airlines and the challenges they encountered early on. Rather than face bankruptcy, the airline had to sell one of its 4 planes, which would force the company to reduce available routes and potentially layoff staff. Instead, the business found a way to be more efficient — drastically reducing gate turnaround time and allowing them to keep all existing routes. Since then, every brainstorm I lead I find a way to make the group’s task slightly more challenging — often by reducing a critical factor like time, budget or another key resource — placing the most obvious path to success out of reach. When I do, I see a level of creativity and problem solving out of individuals and teams that truly astounds me.
Transparency and Trust Go Hand in Hand
A few jobs ago, I had a boss that demonstrated what I call epic transparency. He shared every aspect of the business, from hiring considerations to the company’s financial health — even some personal details that impacted his performance at work. I felt like I was in on some sort of secret and would have done anything to help him or the company succeed.
The transparency he provided and context to the bigger picture has always stuck with me and became something I aim to replicate, especially when working for larger organizations. The majority of employees in a big organization are exposed to the decisions the company makes, but rarely the how or why that decision occured. That leaves them to fill in their own blanks and make assumptions about the direction of the company and the nature of its leaders. When I fill in some of that context, I find the level of appreciation for company leaders and connectivity to their company grows immensely.
“Disagree, But Commit” Doesn’t Always Cut It
In theory, the Jeff Bezos phrase “Disagree, But Commit” is a great way to break through the logjam of a consensus-driven organization. I’ve used it a number of times when leading workshops with external organizational leaders to prevent delays due to indecision. The challenge is that in practice, people are more likely to disagree but dismiss — distancing themselves from the agreed upon direction and not showing interest or support. To ensure that I truly have the buy-in from the dissenting parties, I have them identify what commitment looks like. How will they follow up? What will they own? How can they show support? Even if it’s small, when someone has to define their commitment to a decision they don’t agree with, you know they’re truly along for the ride.
Rituals Are A Powerful Way to Unite People
At Prolific, we’re constantly assembling cross-functional teams of various sizes to address our different client’s needs. In some cases the individuals have worked together before, but more likely I am leading a brand new team and asking them to quickly form a cohesive unit and solve a complicated problem — not an easy task!
I’ve tried out many things over the years to foster team unity, and found the most effective approach is identifying that team’s ritual. For one project, my team celebrated a long week with “Fast Food Friday,” trying a new fast food restaurant every Friday afternoon following a meeting with our client in Fremont. Another time we developed the “Saddest Song List” on Spotify. Each team member would suggest songs for inclusion and we added to it throughout the project. We played it when we had a challenging day and it became the team’s ballad for bonding. Rituals are a way to create a fun, shared tradition that allows each person to uniquely contribute and express themselves.
Imposter Syndrome is Something You Don’t Grow Out Of
For many years, I thought I had Imposter Syndrome because I followed a non-traditional career path (switching industries a few times). While that approach helped me find my true calling and made me a very well-rounded professional, every time I stepped into a new role, I was plagued by the feeling that I was a fraud.
After meeting a number of accomplished female professionals, I realized that Imposter Syndrome is partly a by-product of personal growth. If you’re constantly challenging yourself to try something new — a new role or a new industry — especially as you gain more seniority, you will likely feel that nagging sense of self doubt. Now, I have an easier time when these feelings arise, because I focus on embracing discomfort and doubt as signs that I am doing what I love most — growing.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
A quote I use often in meetings with leadership teams is: “There are no bad decisions, just implications and consequences.” I do that to help a team reach consensus. Often times, the fear of making bad decisions prevents people and teams from making any decision at all. By reframing it this way, I am helping individuals shift to focus on making an informed decision — understanding the pros, potential outcomes and risk. Informed decisions don’t always work out perfectly, but they’re the most critical ingredient in making consistent progress.
Personally, this is an expression I think about a lot when considering a move that makes me uncomfortable. It prevents me from getting hung up on the decision-making itself. As long as I understand the potential implications of a decision, I can move forward knowing that any outcomes are a step forward.
Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why?
I would love to sit down with Hayley Barna, a partner at First Round Capital. She is an entrepreneur who founded cosmetics retailer BirchBox and an all-around badass. I am very interested in hearing how she raised money and got traction as one of the earliest players in the subscription box market.