Mandy Cole

Gusto announced plans to acquire Guideline last week. This is huge news for the recordkeeping sector and a testament to the power of integrated retirement products. This acquisition is a product match made in heaven. Connecting Gusto’s payroll platform and Guideline’s recordkeeping system creates a product-first experience for the plan sponsor: everything they need to set up and manage a plan is readily available in the product. Built-in data connectivity makes plan setup entirely self-serve, which is perfect for most SMBs, who don’t have the time to sit through multiple plan design calls. Combining efforts puts Gusto and Guideline on the path to $1B in combined revenue and sets them up nicely for a future IPO. Gusto will continue to support other recordkeepers through Finch and their partner marketplace because every recordkeeper brings a different value proposition to the table. Some solutions may support complex plan designs or offer high-touch advisory services. Even while offering a first-class embedded experience through Guideline, Gusto is demonstrating the value of supporting employers’ choice in what software solutions they use and the importance of connected experiences, regardless of the provider. Congrats to Josh, Andy, and Tomer at Gusto and Kevin at Guideline.

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C.C. Gong is a principal at Menlo Ventures focused on early-stage consumer tech and SaaS investments. Drawing on her extensive experience as a product leader and team builder, C.C. goes all in on supporting founders who optimize for impact. She believes that personalized AI will revolutionize the next generation of human-computer interaction and how humans live, work, and play. C.C. started her career at Microsoft, where she worked in product at Bing Ads and HoloLens, and ran an incubation team that shipped novel consumer experiences in mixed reality. At Meta, she led teams building the future of search and ranking in its suite of messaging apps. Guided by her passion for mission-driven impact, she left big tech when she was selected as one of 20 top technologists in the nation to serve as a White House Presidential Innovation Fellow, during which she used design thinking to advance service delivery at the United States Department of Veterans Affairs. Following her stint in public service, C.C. joined Bain Capital Ventures, then became NFX’s first Venture Fellow. She also helped run one of AngelList’s most prolific syndicates and scouted for multiple funds, including Menlo and Wing VC. She proceeded to delve deeper into the startup world, leading product and growth at multiple early-stage companies from seed to Series A, as well as launching her own company in the AI video editing space. She knows firsthand how hard it is for founders to get from zero to one, so she created a community and resources for entrepreneurs and hosted five AI hackathons in 2023. C.C. received her bachelor’s degree from Harvard University and her MBA from Stanford University’s Graduate School of Business. In her free time, she loves performing standup comedy, dancing salsa, and hosting poker nights. She grew up in Anaheim, CA next to Disneyland, and went to Disney Elementary School, so theme parks have a special space in her heart. An adventure aficionado, she’s traveled to 80+ countries and has infinite travel hacks to share. Topics: - The intersection of AI and consumer products - What sectors within SaaS are still undervalued or overlooked - How consumer behavior changes are creating new SaaS categories

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🔆 Robert Cabral 🔆 is in the Spotlight today! Robert leads Support & Enterprise Education at Runway. Over the past 10 years, he's built post-sales teams from the ground up at multiple startups, including scaling companies from $5M to $100M+ ARR. He shares insights on support leadership, operations, AI, and more in his newsletter, "Beyond the Queue." 𝗛𝗼𝘄 𝗵𝗮𝘀 𝘁𝗵𝗲 𝗿𝗼𝗹𝗲 𝗼𝗳 𝗰𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝘀𝘂𝗽𝗽𝗼𝗿𝘁 𝗰𝗵𝗮𝗻𝗴𝗲𝗱 𝘀𝗶𝗻𝗰𝗲 𝘆𝗼𝘂 𝘀𝘁𝗮𝗿𝘁𝗲𝗱 𝘆𝗼𝘂𝗿 𝗰𝗮𝗿𝗲𝗲𝗿? When I started, support was seen mostly as a reactive function. While I worked with many talented individuals, there wasn't much room for strategic work. It was about fixing the issue, closing the ticket, and moving on. Today, it has evolved into a key part of the customer journey. The best teams act as partners. They surface insights that influence product, marketing, and revenue. That shift from helping customers to helping the business understand customers is where I've focused most of my career growth. 𝗛𝗼𝘄 𝗱𝗼 𝘆𝗼𝘂 𝘀𝗲𝗲 𝗽𝗼𝘀𝘁-𝘀𝗮𝗹𝗲𝘀 𝘁𝗲𝗮𝗺𝘀 𝗲𝘃𝗼𝗹𝘃𝗶𝗻𝗴 𝘄𝗶𝘁𝗵 𝗔𝗜? We’re living this evolution right now. The real question isn't whether to use AI, but where the handoff between automation and human judgment should happen. Get that wrong, and you create a faster path to frustrated customers. Get it right, and your team can focus on the complex problems that actually require human insight: account health analysis, strategic implementation planning, and turning at-risk customers into advocates. AI is already changing how we work, but the real opportunity is in what it frees us to do. The more we automate repetitive tasks, the more space we create for deep customer conversations, proactive retention work, and relationship building. There's a concern that AI will make customer interactions distant and cold. But I see the opposite happening. Teams will be able to focus on uncovering opportunities that build customer trust and expand revenue. 𝗪𝗵𝗮𝘁 𝗱𝗼 𝗺𝗼𝘀𝘁 𝗽𝗲𝗼𝗽𝗹𝗲 𝗴𝗲𝘁 𝘄𝗿𝗼𝗻𝗴 𝗮𝗯𝗼𝘂𝘁 𝗰𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝘀𝘂𝗽𝗽𝗼𝗿𝘁 𝗮𝗻𝗱 𝘀𝘂𝗰𝗰𝗲𝘀𝘀? Many still view support or success as a necessary cost center. But great support is a growth channel. Every customer conversation is a data point, a retention lever, and an early signal of churn or expansion. When your success team notices a customer's usage dropping off or support spots repeated friction with a specific workflow, those aren't just service issues, they're retention and revenue signals. Address them proactively, and you prevent churn. Ignore them, and you're leaving money on the table. When teams are set up right, aligned with operations, product, and revenue, support can be one of the most strategically valuable parts of a business. That mindset shift is what transforms post-sales from a service function into a competitive advantage. (continued in comments!)

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