Show notes
In this episode of Marketing Spark, Mark Evans sits down with Caren Cioffi, co-founder and CEO of Agenda Hero, an AI-powered platform designed to eliminate manual calendar work and save billions of hours.
After more than a decade at Brightcove, where she helped scale the company from startup to global public enterprise, Caren made the leap into entrepreneurship to solve a problem she experienced firsthand: the hidden time cost of managing schedules. What began as personal frustration with juggling work, travel, and family logistics evolved into a startup tackling one of the most persistent workplace inefficiencies.
Caren explains how Agenda Hero uses AI to convert text, images, and PDFs into structured calendar events across Google, Outlook, Apple and more. She shares how the breakthrough came when AI made it possible to automate tedious form filling that calendars have required for decades.
The conversation also explores:
• How to validate product-market fit before scaling marketing
• Why building a product people genuinely love is the best early marketing strategy
• Lessons learned from pivoting within her own product
• How she approached raising venture funding for the first time
• The role of influencer and advocacy marketing in early-stage growth
• Why founders need conviction and the right believers around them
From the conversation
Leaving Brightcove and the problem behind Agenda Hero
Caren Cioffi joined Brightcove in its earliest days, before the company had any customers. She was there for the first customer and stayed as it grew into a global public company, eventually running the enterprise business unit as EVP and GM. Along the way she became the person who got the blank piece of paper projects, such as a new market or a new geography.
Caren says she always wanted to start something from zero. The idea for Agenda Hero came at lunch with her mentor Katie Rae, who leads MIT's Engine. Asked what she was spending her time on, Caren realized the answer was managing time. She had two busy kids, and both she and her spouse traveled for work, so her Sundays went to working out where everyone needed to be in the coming week.
Even with all that effort, the family was still failing to keep track. Caren concluded that she could not be the only person with this problem and that technology should be able to solve it. Parents, professionals and students turned out to share it.
What Agenda Hero does and how it charges
Caren describes Agenda Hero as an AI platform for dates and times. Its core product, Agenda Hero Magic, converts text, images and PDFs into calendar events for Google, Outlook, Apple or an Agenda Hero calendar. Her examples include a photo of a jury duty notice and dense school calendar PDFs, where multiple events can be converted at once.
The business model is freemium. Most users stay on the free product and can upgrade for more usage and features. Caren first expected consumers to use the free tier while businesses paid, but both groups are paying. The first upgrade costs $30 a year, and businesses can pay that or more depending on what they need. Pricing launched only in the second half of last year.
Caren's advice to other founders, learned at Brightcove, is that pricing and packaging will keep evolving as the product grows.
Why AI made the problem solvable and how the product changed
Caren says calendars have not evolved in decades, and billions of schedules are created each year in Docs, Sheets and PDFs without a calendar invite. Other founders had tried to fix this for 25 years. Dates and times are technically hard because of time zones and recurrence, and even a single event is a form with a title, date, location and description.
The first version of Agenda Hero was a collaborative calendar. Adoption was real, with strangers using it, but it stayed small. When AI arrived, the team added a feature that let users type a sentence and get an event. Users began saying they wished Google Calendar could do that. Caren remembers the exact chair she was sitting in when she asked what would happen if the feature left their calendar and worked with every calendar. That became Agenda Hero Magic.
Caren is not an engineer. She used Lovable to turn her vision into something tangible to share with the team, and she convinced Brightcove alumni to join as the engineering team.
"What AI has done for Agenda Hero is it has eliminated that tedious manual form filling."
Finding the first users and early marketing
For the first users, Caren recommends setting goals she can control. Instead of aiming for 100 users by a date, she aimed for 10 calls, then 20, using introductions from friends and family to people who might have the problem. Every so often someone on a call asked if they could use the product. It was a form of sales, Caren says, but it felt like learning.
On marketing, Caren says she was advised not to spend early and that building something people tell each other about is the strongest approach. If she did it again, she would spend a little on early social, even $20 a day for a week, to see whether the product reaches people outside her network. She now runs a $30 a day social test, but otherwise growth is organic. Awareness and distribution are still the biggest thing she is working on.
Caren has been studying how AI startups grow and sees influencer marketing as a real spend, though so far hers has been organic. Mark prefers advocacy marketing, where trusted people recommend a product without needing a huge audience. Robbie Fowler's newsletter led Mark to Agenda Hero, and Jeremy Kaplan recently listed it alongside NotebookLM and a Canva AI product among five tools. Caren had not met either of them.
Mark suggested contacting tool curators, and thanking advocates while asking how they found the product, what they like, what to improve and where else to share it. Caren said she plans to start doing that.
"The marketing plan was build the best product that the world loves. So that actually was the marketing plan."
Raising venture funding for the first time
Agenda Hero is not bootstrapped. Mark noted that Upfront Ventures, K9 Ventures and Precursor have backed it. Raising money was new to Caren and a steep learning curve, but she treated it like any other goal and worked it out.
She also changed how she thought about it. At first she saw fundraising as getting the money. Later she saw it as building a team, because an investor joins the company the way an engineer or a marketer does. Looking for someone who believes in the problem and the solution let her use her experience recruiting.
Mark added that early-stage investors back people as much as ideas, and Caren's track record at Brightcove likely helped.
"The thing that I learned in fundraising is you just need one believer. So it's okay if funds are not at the right place at the right time to invest in you."
Advice for founders and what comes next
Asked what she would tell herself at the start, Caren points to conviction and the people around her. The hardest part of being a founder, she says, is that even someone with product, marketing, sales and partnership skills cannot do it all at once. She recommends focus days, with time for strategy separate from time for execution.
Caren says her whole team now uses AI to move faster, and she names Lovable and Claude as favorite tools. She believes the world is still early in using AI. Next, she wants the next billion schedules to be created inside Agenda Hero, so they are structured from the start and need no conversion. Listeners can find her on LinkedIn or at agendahero.com, and she says she reads every email.
"I would say surround yourself with your believers. There will be a lot of people who doubt because most people don't have the ability to see what doesn't yet exist."