Reclaim.ai is a leading AI calendar app that recently launched a feature called Smart Meetings – which is the solution on the market that can automatically schedule and reschedule recurring meetings at the best time for everyone. Pulse 2.0 interviewed Reclaim AI co-founder and COO Henry Shapiro to learn more about the company.
Henry Shapiro’s Background
What is Henry Shapiro’s background? Shapiro said:
“My background is primarily in product management. I’ve worked at large, hyper-scale companies like New Relic, leading product and marketing teams and growing revenues from $100 million to $500 million through IPO. I’ve also worked for smaller companies and startups as a product leader.”
Formation Of Reclaim AI
How did the idea for Reclaim AI come together? Shapiro shared:
“Reclaim was created after my co-founder, Patrick, and I experienced firsthand the challenges of managing time and competing priorities across large, distributed teams. The goal of Reclaim is to make the calendar smarter so that it can make decisions the way humans do about where time should be spent. Not only does this help individuals with their time management and productivity, it also assists teams and companies with aligning their priorities to their efforts, and with solving their most complex scheduling challenges.”
Favorite Memory
What has been your favorite memory working for the company so far? Shapiro reflected:
“I think our first launch is the thing that really sticks out to me. It was a simple feature that allowed people to sync their personal calendars to their work calendars to prevent overbookings, and it’s how Reclaim got its first 5,000 users. We learned a lot from that experience, namely that to do this job well, you have to earn the trust of users by doing lots of little jobs for them at the start of their experience. We continue to use Calendar Sync as a feature to help introduce people to AI scheduling and automation.”
Core Products
What are the company’s core products and features? Shapiro explained:
“Reclaim.ai is an AI calendar app that automatically finds the best time for meetings, tasks, habits, and breaks around your existing calendar. Designed for individuals, teams, and enterprises, Reclaim helps you automatically align your time to your top priorities and solve complex scheduling challenges that cost you time every week.”
“We offer a full suite of features for managing the holistic set of events on your calendar. You can use features like Habits and Tasks to create time for heads-down work that adjusts in real-time (in the same way Smart Meetings do). You can also use our Scheduling Links to send prioritized availability to potential customers and prospects. Additionally, we offer features for automatically creating buffers between meetings for breaks and travel, syncing calendars to prevent overbookings, color-coding your calendar based on intelligently-detected categories, and more.”
“Our newest feature, Smart Meetings, uses patent-pending intelligence and machine learning to automatically schedule your workweek. It does this by allowing users to define rules and preferences for their time. It can then take action in real-time as things change on the schedule or as the user’s priorities change. Smart Meetings extends this technology to multi-person recurring meetings. Anyone can take an existing recurring meeting and allow Reclaim to automatically schedule it around a variety of complex rules and algorithms.”
Challenges Faced
What challenges have Shapiro and the team faced in building the company? Shapiro acknowledged:
“Like all software businesses, we have experienced the contraction in IT budgets and software budgets eating into our ability to close and grow revenue. That said, the past year has been our fastest-growing period thus far, and we’ve managed to close our largest-ever enterprise customers by hooking into existing budgets, consolidating spend, and proving value via ROI benchmarks and analysis.”
Evolution Of Reclaim AI’s Technology
How has the company’s technology evolved since launching? Shapiro noted:
“Our tech stack is fairly simple but involves developing proprietary algorithms and models that are constantly being refined to address user challenges and needs. Our real-time scheduling engine is the only one of its kind in the market, responding in changes to the schedule within seconds of them happening and re-evaluating the entire calendar based on even small inputs. That backbone capability is what we’ve built around, adding modules to it for things like defining time policies (when things should happen within flexible time periods), defensiveness (how aggressively Reclaim should defend time on the calendar based on priority and availability), and prioritization. What we’re building is incredibly complex and has a ton of nuance associated with it, and we have evolved our tech stack to meet those demands.”
Significant Milestones
What have been some of the company’s most significant milestones? Shapiro cited:
“We’ve made a ton of progress on our vision and delivering value to our customers over the past 5 years, but the big milestones that stick out are our Priorities launch, which introduced (for the first time) a native concept of priorities associated with calendar events, allowing us to unlock true AI scheduling for our users and streamline scheduling negotiation. The second that followed soon thereafter was the launch of Smart Meetings, which opened up Reclaim to automate meeting scheduling for any flavor of recurring meeting.”
Customer Success Stories
After asking Shapiro about customer success stories, Shapiro highlighted:
“Yes! Our customers are always sharing their feedback and successes from using Reclaim.”
“‘As someone who spends a lot of time with customers and also needs to coordinate meetings with my team internally, I’ve got a lot of meeting pressure on my calendar,’ says Julian Rost, Engineering Lead at Seibert Group. ‘Discovering Reclaim transformed my approach to time management and got me back 5 to 10 hours a week in just struggling to manage my schedule. With Smart Meetings, I’ve freed up those hours for productive problem-solving and customer-focused work because I don’t need to worry about coordinating meetings anymore.'”
Funding
When asking Shapiro about the company’s funding details, he revealed:
“Reclaim has raised $13 million to date across multiple funding rounds and has over 13,000 paid customers.”
Total Addressable Market
What total addressable market (TAM) size is the company pursuing? Shapiro assessed:
“We believe that the total market for Reclaim cuts across a variety of existing segments, including scheduling ($1 billion to $2 billion in annual spend), project management ($50+ billion in annual spend) as well as team and meeting management (e.g., transcription services, agenda automation, OKR platforms, etc.) which has another several billion in annual spend.”
Differentiation From The Competition
What differentiates the company from its competition? Shapiro affirmed:
“This is the first solution that actually delivers true intelligence for meeting scheduling, solving one of the biggest problems in teams and enterprises. What’s unique about Reclaim’s approach is its use of priorities and context to know when meetings can be adjusted, negotiated, or rescheduled – and when they can’t.
Future Company Goals
What are some of the company’s future company goals? Shapiro pointed out:
“Our plan is to also start to own one-off meetings, which are incredibly complex to schedule across multiple busy people. For Smart Meetings specifically, we are planning to introduce even more intelligence to our algorithms so that we can learn from historical meeting patterns and prescribe or suggest changes to the user’s priorities and preferences – and take action on their behalf.”
“What we get excited about is the future where Reclaim – a world-class scheduling engine with years of intelligence and development – is married with world-class LLMs to help automatically interpret what’s on the calendar and take action. Our users and customers are hungry for a true AI agent for scheduling, and we believe we’re the best equipped to deliver it for them.”
Additional Thoughts
Any other topics you would like to discuss? Shapiro concluded:
“Smart Meetings was just launched and came after we found, within a proprietary study of 1,300 professionals, that the average professional spends 14.8 hours a week in meetings and up to 3 hours a week scheduling and rescheduling their meetings.”
