The Dave Gerhardt Show: From Growth Marketer to CMO—How Kelly Cheng Leads Marketing at Goldcast

Date: October 23, 2025
Host: Dave Gerhardt
Guest: Kelly Cheng, CMO at Goldcast

Episode Overview

In this engaging episode, Dave Gerhardt sits down with Kelly Cheng, the Chief Marketing Officer at Goldcast, to unpack her remarkable journey from growth marketer to CMO. The conversation covers Kelly's unique career path, building a dynamic marketing organization, transitioning from product-led to sales-led motion, the significance of mentorship, navigating brand vs. demand, running large marketing teams, Goldcast’s operating system, and what’s really working in B2B marketing today. Both transparent and tactical, the discussion delivers valuable advice for marketers aspiring to grow into leadership roles while balancing life and parenthood.

Key Discussion Points & Insights

1. Kelly’s Background & Career Journey

• Global Upbringing and "Camp" in Connecticut:
  Kelly shares she was born and raised in Hong Kong, coming to the US solo for boarding school at 14 and later attending Boston College.
  “My parents shipped me off as soon as I became a teenager, which was smart.” (03:01, Kelly)

• Early Marketing Experience:
  Started in growth and performance marketing at agencies, then transitioned into tech at PagerDuty in San Francisco—where she developed an experimental, product-led marketing mindset.
  “I was doing growth on the product side with the trial, but also running demand generation with the sales LED funnel.” (09:03, Kelly)

• Joining Goldcast & Evolving with the Company:

  • Joined as growth lead and shifted quickly to running marketing due to the unique challenges of a PLG events platform.
  • Drove the move from product-led to sales-led when user errors started impacting perceived product value.
  • Celebrated four years at Goldcast, now leads a team of 30.

2. Mentorship & Navigating the Transition to CMO

• The Value of Mentors:

  • Kelly credits much of her growth to having strong mentors (Rebecca Klein from PagerDuty and Sydney Sloan from G2), both of whom provided crucial support on executive presence, negotiation, personal challenges (even first to hear of her pregnancy!), and transitioning to CMO.
    “Having her gone through. Having experience, gone through all this in the past, herself personally guiding me through it was extremely helpful. So I'm forever grateful.” (13:08, Kelly)
  • Founders at Goldcast actively sponsored/connected her to mentors and advisors, e.g., Sydney Sloan and former Twilio CMO Francois.

• Advice on Finding a Mentor:
  "It starts with, like, coffee chats. You can't just, like, force a mentorship. It has to work in terms of two people jiving and having some common ground. So it's kind of like dating almost." (15:19, Kelly)
  LinkedIn and communities like Exit Five's CMO Council are excellent places to begin.

• Shifting Skills from Growth to CMO:

  • The leap to CMO requires embracing people management, executive business acumen, and the patience for long-term results—not just running programs.
  • Managing a team of diverse personalities & backgrounds (now 30+ across the globe) is a whole new challenge. "Going from managing programs to now being a CMO. I manage a team of 30 full time and freelance contractors and many agencies and globally worldwide and remote. That was a huge, huge jump." (10:43, Kelly)

3. Questions to Ask Before Taking a Marketing Leadership Role

Kelly shares what she wishes she knew, providing actionable, CMO-vetted interviewing advice:

• Long-Term vs. Short-Term Appetite:
  “I would want to vet for the appetite to invest in long term marketing bets versus just short term... The value of marketing is a long lasting brand that helps you get to that trajectory." (20:56, Kelly)

• Budgeting, Finance, Company Culture:
  Ask how founders think about marketing budgets, planning cycles, and the alignment between finance and marketing. Also, dig into the company's culture and communication style—things she never considered in her early interviews but now views as vital. "I also never asked about, you know, their, their company culture vision, like how like, you know, I was so eager to jump into something new that I never even considered...their communication styles." (23:37, Kelly)

• Understanding Funding & Pressure:
  Knowing the company’s financial runway changes what’s possible and the risks you can take as CMO (see: Drift’s early $15M raise gave them freedom to build foundationally).

• What It Means to ‘Sit at the Exec Table’
  “Your job becomes not just to manage marketing, but you're truly an executive and you have a seat at the leadership table…you have to understand the full picture of the company, not just what's going on in marketing.” (25:18, Dave)

4. The Goldcast Marketing Org & Operating System

Org Structure & Roles

• Direct Reports:
  • Senior Director of Product Marketing (product launches, messaging, customer stories)
  • Director of Content (brand strategy, creative, SEO, communities: Event Marketers Club, AI Marketing Alliance)
  • Director of Growth (demand gen, pipeline, BDRs; BDRs now under marketing)
  • Director of Events (field & event strategy)
  • Marketing Operations

Team Scorecard, OKRs & Metrics

• Three Main OKRs:
  1. Building Mindshare (top-of-funnel brand and product usage showcase)
  2. Pipeline-Driven Targets (revenue sourced/attributed)
  3. Efficiency (tool consolidation, process improvements, internal productivity)
  • Brand affinity and mindshare are measured using organic search, referral traffic, direct response, and market “buzz.”

Operating Rhythm

• Mondays: Set up week, cross-functional catch-ups
• Tuesdays: Weekly marketing leadership call (directs) in Notion (no decks), weekly pipeline meeting w/ sales & RevOps
• Wednesdays: 1:1s with all direct reports—used for their benefit and to clear blockers
• Once a month: skip-levels with all team members (20–25 minutes, candid, no agenda)
• "If you don’t own your calendar, your calendar owns you." (36:03, Kelly)
• Transparency and open communication help avoid being out of touch as a leader.

5. Brand vs. Demand—The Case for Mindshare

• Measuring Brand/Mindshare:

  • Brand affinity is “hard to quantify,” but key indicators include brand search volume, direct traffic, and LinkedIn/online chatter.
    “A lot of people think mindshare equals brand. They're not... only 5% of your target audience is ever in the market to buy… you have to build that runway." (33:43, Kelly)

• Boardroom Challenges:

  • Executives want to see direct revenue impact—why do we have two video producers, what’s the ROI? Kelly notes the need to defend long-term plays. “You can just feel when people are talking about us online. That’s got to have a downstream effect … but for some reason, we can’t use that logical brain when it comes to measuring marketing.” (32:06, Dave)

• Choosing Founders Who Get It:
  Having founders who value non-directly-attributable marketing (even if imperfect) is essential to building a strong, modern brand.

6. Sales & Outbound: BDRs in Marketing & What’s Working Now

• Moving BDRs Under Marketing:
  “I see Outbound as a pipeline lever that we're really not taking full advantage of. And I wanted to bring that onto the marketing side…” (41:00, Kelly)

  • BDRs leveraged for campaign follow-up, tighter alignment, and pipeline generation.
  • Bringing outbound, brand, and demand together made cold outreach more effective.

• Making Outbound Actually Work:

  • Combining tooling (e.g., Qualified for intent, Vector for de-anonymizing site visitors, Clay for data enrichment), close alignment with content, and relentless focus on data quality.
  • Outbound still works—phone calls set plenty of meetings. “Phone calls still work really well. I know this because we started working with an outsourced SDR team about a month ago, and they purely do phone calls, and they've booked so many meetings through the phones.” (44:36, Kelly)

• Outbound Success Keys:

  • Deep ICP understanding and sharp messaging—calls must instantly hit relevant pain points.
  • Quality over quantity: "It's asking an opening question that gets them to bite and then engage in a conversation." (45:10, Kelly)

7. Content, Community, and Measurement

• Live Content → Repurposing Engine:

  • Goldcast eats its own dog food: run live webinars with top marketing experts, then repurpose into micro-content, blog posts, assets, and distributed through their communities.
  • Communities serve as qualitative and engagement data hubs.

• Attribution & Measurement (Still Hard!):
  "Sort halfway, it's half baked. I feel like any marketer that tells you they figured it out is lying to you." (49:03, Kelly)

  • Founders’ trust in the process allows investments in brand/content/community even if attribution isn’t perfect.

8. Biggest Current Marketing Challenge

• Unifying the Buyer Org & Product Messaging:
  As Goldcast repositions from point solution to platform, the key challenge is aligning & communicating value across highly siloed personas (e.g., event marketers, content creators, demand gen). "A thing I'm looking to solve for is how to bring all those people together so we can help them consolidate tools... Oftentimes they're even using different project management tools so they don't talk to each other." (50:31, Kelly)

9. Leadership, Parenthood & Vulnerability

• Balancing CMO & Parenthood:
  • Returning from maternity leave was the “single most challenging year” of her life; taught her to let go of needing to have all the answers. “I've really let that go a bit, that, that expectation for myself...I've done everything humanly possible to prepare my team, but there's only so much I can control and just, it's really recognizing that and finding boundaries for myself.” (52:14, Kelly)
  • Emphasizes growth, vulnerability, and boundaries as a marketing executive and as a parent.

Notable Quotes & Memorable Moments

• “You can't just, like, force a mentorship. It has to work … It's kind of like dating almost.” (15:19, Kelly)
• “If you don't own your calendar, your calendar owns you.” (36:03, Kelly)
• “Only 5% of your target audience is ever in the market to buy... But you still have to engage with them, because once they are in market to buy...it's too late, because they don't know who you are.” (33:43, Kelly)
• “Phone calls still work really well... They've booked so many meetings through the phones. And so it's my mission to figure out how we can get our phone numbers right.” (44:36, Kelly)
• “I've always blended personal and professional because I care so deeply about my reputation at work...But it's really trying to find those boundaries wherever I can.” (53:39, Kelly)

Timestamps for Important Segments

| Time | Segment | |---------|-------------------------------------------------------------------------------------------------------------------------| | 03:26 | Kelly’s background—Hong Kong to Boston, early career | | 04:58 | Joining Goldcast; from growth lead to CMO | | 09:39 | What changes going from growth to CMO | | 12:24 | Mentorship & the value of sponsors | | 20:56 | Interviewing advice for marketing leadership roles | | 28:11 | Goldcast marketing org structure | | 30:08 | Scorecard: Mindshare, pipeline, efficiency objectives | | 35:47 | Operating system: calendar, meetings, 1:1s, skip-levels | | 41:00 | Moving BDRs under marketing; outbound lessons | | 44:36 | Outbound experiments; phone calls are working | | 47:29 | Content as the engine—webinars to repurposed assets & community | | 49:03 | Attribution, measurement, and founder trust | | 50:31 | Biggest marketing challenge: uniting personas for platform positioning | | 52:14 | On motherhood, vulnerability, boundaries, and setting up the team before leave |

Final Thoughts

This episode offers a rare, honest look behind the curtain at both the practical mechanics and the emotional side of being a CMO today. Kelly’s journey showcases the importance of evolving skills, embracing mentorship, aligning with leadership that truly “gets” marketing, and building an organization that can thrive whether you’re at the office or on parental leave. For ambitious marketers, her story is equal parts playbook and pep talk.

Connect with Kelly on LinkedIn (and help her get to 10K followers!):
https://www.linkedin.com/in/kellycheng