Ignite Startups: Leveraging Direct Mail and AI to Build a Global Company with Kris Rudeegraap
Episode 105 of the Ignite Podcast
When it comes to building lasting relationships with customers, finding ways to stand out can make all the difference. Kris Rudeegraap, co-founder and co-CEO of Sendoso, has mastered this art through a unique blend of corporate gifting and technology. In this podcast interview, Kris shared his entrepreneurial journey—from founding a college startup to leading a global corporate gifting platform. For those who might not have time to listen to the episode, here's an in-depth look at some of the valuable insights and lessons from Kris’ experience.
The Early Days: From Student Rentals to Sendoso
Kris’ first foray into entrepreneurship started while he was still in college. He founded All Student Rentals, a platform designed to solve the problem of finding off-campus housing. Inspired by the booming Silicon Valley tech scene, Kris realized there was a better way for students to find housing than relying on platforms like Craigslist. This venture taught him the fundamentals of running a business, raising money, and scaling a solution to a real-world problem. Though his first company was eventually sold to Yapstone, the lessons he learned from building a company as a student laid the groundwork for his future success.
One of the key takeaways from Kris’ early experience was the importance of solving a problem that truly resonates with your target audience. His experience at All Student Rentals gave him the confidence to tackle bigger challenges, and it led him to his next venture—Sendoso.
The Birth of Sendoso: An Idea Born from Sales Frustration
Before founding Sendoso, Kris spent over a decade in sales roles at various software companies. During this time, he observed the increasing saturation of email marketing and customer outreach. With declining open rates and engagement, Kris needed a way to break through the noise.
What started as a simple strategy—sending handwritten notes, swag, and even dog toys to potential clients—quickly became a powerful method for building customer relationships. Kris realized that direct mail and corporate gifting were incredibly effective, but also time-consuming and operationally challenging. That’s when the idea for Sendoso was born: a platform where companies could send personalized gifts and direct mail with just a click of a button.
Solving a Complex Problem with Technology
Sendoso was built to make gifting easier, scalable, and more integrated into modern sales and marketing tech stacks. While many companies were already doing corporate gifting, Kris knew that Sendoso could differentiate itself by leading with software. The platform integrates with tools like Salesforce and Marketo, making it easy to automate sending gifts based on customer engagement data. This approach transformed Sendoso from a simple gifting service into a full-fledged demand generation and customer engagement tool.
One of the platform’s early success stories came from Kris himself, who used it to engage prospects when traditional email outreach wasn’t working. The personalized touch of sending physical gifts helped businesses create deeper connections with their customers, increasing brand loyalty and driving revenue. For example, a company could send a custom gift after a successful meeting or as a surprise thank you, reinforcing the relationship and keeping the company top-of-mind.
Scaling a Global Platform: Challenges and Successes
Like many successful startups, Sendoso’s growth wasn’t without its challenges. From managing global warehouses to navigating the logistics of shipping gifts internationally, Kris and his team had to build a robust operational infrastructure. The company raised multiple rounds of funding—eventually securing a significant investment from SoftBank—to scale its operations and expand into new markets.
Despite the logistical challenges, Kris believes that Sendoso’s software-first approach has been its secret sauce. The ability to offer thousands of curated gifts from global vendors, automate the entire process, and track results through data and AI has given Sendoso a competitive edge. By focusing on seamless customer experiences and operational efficiencies, Sendoso has become a leader in the corporate gifting space, with over $250 million in sales on the platform and tens of millions of items sent.
The Role of AI and the Future of Gifting
Looking forward, Kris sees AI playing an increasingly important role in Sendoso’s future. The platform has already integrated features like Smart Send and Smart Messaging, which help customers send the right gift at the right time with the right message. These AI-driven tools make corporate gifting more personalized and effective by leveraging data insights.
Kris envisions Sendoso becoming as ubiquitous as email or CRM systems like Salesforce. The gifting space, while large, is still fragmented and ripe for innovation. By focusing on software and data, Kris believes Sendoso can continue to lead the charge in transforming how businesses build relationships through gifting.
Leadership and Lessons for Founders
Kris also shared valuable insights on leadership and scaling a company. As Sendoso grew from a handful of employees to over 200, Kris had to adapt his leadership style. One of the key lessons he emphasized was the importance of transparency and clear communication. As the company shifted from a growth-at-all-costs strategy to a more sustainable, profitable model, Kris made sure that his team understood the reasons behind each strategic decision. He used global all-hands meetings, open forums, and clear OKRs (Objectives and Key Results) to keep everyone aligned and engaged.
He also highlighted the importance of customer obsession. Even after eight years of running Sendoso, Kris continues to meet with customers regularly. His advice to other founders is simple but powerful: always be talking to customers. Whether you’re just starting out or scaling a hyper-growth company, listening to your customers is crucial for staying relevant and delivering value.
Conclusion: The Power of Thoughtful Gifting
Kris Rudeegraap’s journey from student rentals to leading a global corporate gifting platform is a testament to the power of solving real-world problems with innovative solutions. Sendoso’s success comes from its unique blend of operational efficiency, software integration, and customer obsession. As Kris looks to the future, he sees AI as a key driver in making corporate gifting even more personalized and impactful.
For founders, sales professionals, and business leaders, Kris’ story offers valuable lessons in scaling a business, building strong customer relationships, and leading with transparency and vision. If you’re looking for ways to stand out and create lasting connections with customers, corporate gifting might just be the strategy you need.
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Chapters:
· Introduction to Kris Rudeegraap & Sendoso (00:01 – 00:45)
· Kris’ First Startup: All Student Rentals (00:45 – 02:55)
· Transition to Sendoso: From Sales Frustration to Gifting Solution (02:55 – 06:31)
· The Birth of Sendoso and Early Growth (06:31 – 09:27)
· Scaling Sendoso: Customers, Venture Funding, and Operations (09:27 – 11:19)
· Overcoming Operational Challenges and Global Expansion (11:19 – 15:35)
· Sendoso’s Leadership Structure: Co-CEO Model (15:35 – 18:14)
· Building Company Culture at Sendoso (18:14 – 19:47)
· Customer-Centric Growth: The Importance of Obsessing Over Customers (19:47 – 22:12)
· Sendoso’s AI and Data Innovations (22:12 – 28:54)
· Long-Term Vision for Sendoso: Becoming the Salesforce of Gifting (28:54 – 30:40)
· Lessons Learned: Retention, Expansion, and Customer Focus (30:40 – 32:02)
· Rapid Fire Questions: Productivity, Best Advice, and More (32:02 – 38:17)
· Closing Thoughts and Where to Find More About Kris & Sendoso (38:17 – 39:06)