Kelly Cheng has been a creative problem solver, marketer, and pitch person for most of her life. She’s circled the globe from Hong Kong to Boston to San Francisco and back, managing an international team today as the Head of Marketing & Growth at Boston based hybrid events platform Goldcast.
Kelly grew up in Hong Kong, the second of four children to her father who was a Boston College Eagle and manufacturing executive. Kelly’s mother hailed from the Bay Area. She has two sisters and one brother who all work in tech. The Cheng kids were trained how to advocate for themselves and each other from an early age. When the siblings wanted a dog, they had to put together a powerpoint presentation to showcase their plan for taking care of it. Who would be responsible for what? How would they delineate the duties? If you wanted something in their family, you had to make a good business case for it! Kelly is a high performer who’s no stranger to giving a good pitch.
But she’s gone through her share of challenges too. As a child she was initially enrolled in a local Chinese school while growing up in Hong Kong. Classes were taught in Chinese but English was Kelly’s first language. She made a name for herself with all the creative ways she would try to get out of going to school. One time she even pretended to lose her vision. Kids do funny stuff! But Kelly certainly had vision, in spades.
She made the move to the international schooling system and really began to excel, unlocking her creativity and talents. She returned to the U.S. for high school and attended a prep school in Connecticut. She loved the high touch academic environment and became determined to get good grades. Kelly tells me she’s always been very independent and this immersive environment felt like summer camp. All of her peers came in together for the 9th grade and some of her best friends to this day are all from high school. Aren’t we all trying to find that summer camp feeling?
Kelly always admired her dad and wanted to go to Boston College just like him. She loved the campus and high caliber academic environment. It’s a foregone conclusion that she got in! At BC she majored in Communications with a specialty in Marketing. She sort of always knew she wanted to be in advertising and…had the vision to know she was more the working type than the academic type. Sorry, I had to do it! While at BC she had full time internships at advertising agencies beginning her sophomore year all the way through graduation.
Coming out of school, she began her career at an advertising agency in Cambridge focused on B2B Marketing called PJA Advertising + Marketing. Still a relatively new field, most of their clients were focused on print ads and trade publications. It wasn’t super sophisticated stuff but the world was changing. Kelly learned about “account based marketing” and leaned into this new digital marketing transformation.
How did she find her PJA role without a large Boston community of connections to rely on? She called on them. Graduating in the summer of 2012, with our economy still slowly recovering from the recession and her parents back in Hong Kong, Kelly was determined to find a job to stay in the U.S. She remembers she probably sent 100s of cold emails with her resume.
Kelly figured out templatized emails only got her so far. She needed to personalize her messages. She learned that finding people on LinkedIn and sending them a message there as an additional touchpoint really helped response rates. It wasn’t easy, but persistence was key.
At PJA she covered media buying, creative and account management fully focused on B2B for clients on the East & West coasts. It was long hours and she eventually went over to another agency, AMP Agency, where she focused on luxury & CPG clients across some 7 customers broadening her exposure to different industries.
She transitioned from an Assistant Media Planner to a Media Planner to a Supervisor, putting in the time to move up as rapidly as she could! Her next role took her to Havas. There, she was focused on a smaller number of clients and got the chance to build her first team and implement a strategy. She worked closely with Fidelity across their different lines of business with various marketing challenges across retail, institutional, and some of their corporate non-profit efforts focused on supporting a sophisticated attribution model.
At Havas, Kelly transitioned to marketing liquor brands including Macallan and Remy Martin where she realized she was ready for a bigger and different type of challenge. She decided to pivot her career and leave her position without another role lined up. It was scary but ultimately the right thing to do. She headed to San Francisco with the hope of landing an “in house” startup marketing role.
Luckily her sister and grandmother were out in the Bay Area so she had a small launchpad for her fresh start. Of course she referred back to her tried and true methodology of cold calling, interviewing, and of course..handling some rejection. Kelly learned to tell her story and properly position herself for the agency > “in house” transition.
Through a cold call and then LinkedIn message she landed at rapidly growing PagerDuty as a Senior Marketing Specialist. She leveraged all the skills she’d gained over the years from her agency experience and applied it with enthusiasm. Kelly created a larger position for herself by learning marketing software tools like Salesforce, Marketo, and scaling up on how a startup GTM machine really works, the world of MQLs, and everything in between.
PagerDuty is where she believes she learned the most of all her previous professional experiences. She was a sponge! She went in humble and eager to prove that she had the analytical chops, could contribute to team quarterly business reviews & more. It also helped that PagerDuty was growing extremely fast. She entered the company right as it announced its Series C and grew with the company through its IPO.
Eventually, Kelly was ready to move back to Boston. She had an unbelievable experience in San Francisco but was in a long distance relationship at the time (to her now husband) and missed that dirty water. Kelly had spent some time in Boston for undergrad but she really fell in love with the city over the years that followed. She lived in a bunch of different neighborhoods all over the city and found Boston to be manageable & charming with a lot of character. She had a lot of friends in the area from high school and BC so it had always felt like a second home. From a Boston startup community standpoint, she loves that she’s been able to cross paths with people repeatedly over the years. Kelly & her husband also have two Australian shepherds that they like to get outside as much as they can in the New England area. The North Shore beaches and Kennebunkport are two tried and true favorites.
When Kelly returned to Boston she joined Dynatrace, a large enterprise business & partner of PagerDuty. This experience helped her see that she thrived in growth company environments where she can work on a bunch of different things and soon joined Cambridge based Wistia.
Wistia was a memorable experience and gave Kelly her first opportunity to market to marketers. Wistia had a similar product led growth GTM motion to PagerDuty and Kelly dove in to apply her previous learnings. But it’s never that simple. Two weeks into her new role, the pandemic hit. For a company building video marketing tools, they hit their yearly growth goals within a month! It was a blessing in disguise and an unbelievable training ground to figure out how to monetize all those freemium users by experimenting with pricing strategies and user experiences across various parts of their funnel.
Kelly worked on a team of 2 growth marketers when she first saw the Goldcast product and was serendipitously approached by a recruiter. Goldcast was looking for a Head of Growth and Marketing. We now know Kelly is no stranger at jumping on big opportunities when they arise. It was a perfect fit and culmination of all her skill building over the years.
It was time to build her first in-house team. From scratch. Kelly’s first priority when she joined was to build out Goldcast’s Marketing team. She started from first principles about what this hybrid events platform, marketing to B2B marketers, would need. It was her sweet spot so she knew that Goldcast needed to have the best events. They also needed to be able to produce stellar content. Some of Kelly’s mentors like Rebecca Kline from PagerDuty helped her hone that strategy over those first days.
Kelly hired a Head of Events and a Senior Content Marketer to support her initial vision which has really paid off. Goldcast is no stranger to the current difficulties across tech and they’re not immune either. In order to support their growth plan, Kelly is focused on finding the right pipeline and revenue opportunities with appropriate budgets to drive continued growth. The biggest challenges are increasing activity but also lowering CAC while thoughtfully scaling the team. Expectations are always on the rise!
In the months ahead, Kelly & her team are focused on gathering continuous feedback, leveraging freelancers, and working efficiently across time zones. More than half of Goldcast’s team is based in India and this is her first time managing an international team. She’s amazed by her team’s work ethic and resilience. Still, managing across time zones is a challenge. Their India team works EST hours and they’ve had to climb the learning curve together to figure out how to best communicate and work collaboratively. It’s a constant learning process.
Here are four learnings Kelly shared with me on her path across the world from agency life to “in house” B2B technology marketing:
Experiment Relentlessly – “At PagerDuty I ran a lot of experiments hiding golden nuggets in internal sales emails like ‘first person that responds gets a $200 gift card’. If you can’t get the outcome you want, experiment thoughtfully and creatively until you begin to see progress.”
Ask For Help – “I was always afraid to ask for help in my agency days because sometimes there wasn’t a lot of help around. I learned to get over that as I progressed in my career because it takes a village to get a project off the ground and putting all the pressure on myself wasn’t healthy or generated a good work product.” It’s something she’s still learning but in a growth stage company cross functional support is essential
No Regrets – “When I left the agency side it was a high risk decision where I didn’t know what was going to happen but I don’t regret that move. Even when I went to a big company for a short period of time I don’t regret that either because I learned I like smaller company environments better. There’s a lot of pressure to make the right decision but regardless of the decisions you make you’ll gather essential learnings”
Building Trust Through Relationships – “Communication and building trust has been super key so that our team feels comfortable sharing feedback. There’s something to be said for getting to know the human being behind the work and investing in those relationships in order to build trust.”
Kelly loves growth stage startup environments. She thrives in the chaos..even if it can sometimes drive her crazy. Her wheels spin fastest when there are problems to be solved. Eventually, she would love to be a CMO at a startup and help a company grow from the mid stage through a successful exit. The chance to continue to build out talented teams accomplishing lofty goals is “what it’s all about”. Basically, exactly what she’s doing at Goldcast! Their team has a lot to accomplish and she’s enjoyed the company building process of becoming a strong people manager who helps motivate her team to accomplish big things. Problem solving keeps her going.
If you’d like to get in touch with Kelly, you can find her on LinkedIn, at a New England dog park somewhere with those Aussie shepherds, or hosting a kick ass hybrid event across the startup ecosystem. Thanks for sharing Kelly. Excited to see the heights you bring the Goldcast team and the events you power across the tech industry in the years ahead!