The CEO’s Guide to Transforming Thought Leadership into Sales Success
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Shownotes
In this episode of OnBase, host Chris Moody talks with Kris Rudeegraap about innovative approaches to thought leadership, the use of AI tools, and leveraging direct mail to break through email saturation and create personalized customer experiences. Kris shares his journey from Silicon Valley software sales to founding Sendoso, a category-defining direct mail and gifting platform. The conversation dives into actionable strategies for building a thought leadership culture, using AI for smarter engagement, and orchestrating complex sales processes. Kris highlights how combining creative campaigns, social media, and direct mail can generate significant pipeline growth and enhance brand awareness.
Best Moments
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Kris introduces his entrepreneurial journey, from selling mistletoe as a kid to founding Sendoso.
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Why thought leadership matters for educating the market and generating leads.
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How AI tools like ChatGPT and customer interviews can refine thought leadership.
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Leveraging direct mail and creative campaigns to stand out in B2B sales.
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Kris shares top AI tools revolutionizing sales enablement.
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The biggest challenge in B2B sales: orchestrating complex sales processes.
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A behind-the-scenes look at Kris’s favorite direct mail campaign: Halloween-themed piñatas.
About the guest
Kris Rudeegraap is the co-founder and CEO of Sendoso, the leading Sending Platform. Kris has more than a decade of sales experience and has spent time at Talkdesk, Yapstone, and Piqora. During that time, he discovered that creating meaningful engagements through direct mail and gifting was an effective way to drive demand and increase sales—which helped inspire the idea for Sendoso. Kris is a California native and CSU-Chico alum currently residing in the Bay Area.
Key takeaways
- Thought Leadership as a Growth Driver: Kris emphasizes the role of thought leadership in educating the market, inspiring internal teams, and generating quality leads.
- The Power of Direct Mail: Innovative direct mail campaigns, integrated with social and digital channels, can cut through saturated email inboxes and create memorable customer interactions.
- Leveraging AI for Sales Enablement: Kris outlines how tools like Clay, Hyperbound, and Grace are revolutionizing outreach, training, and account management.
- Category Creation: Educating the market is critical in emerging categories. Thought leadership and community building can amplify this effort.
- Social Media for Pipeline Growth: Consistently sharing content and creating employee-driven advocacy on platforms like LinkedIn can be a lead generation powerhouse.
Quotes
On Thought Leadership:
“Thought leadership inspires your team internally and builds trust externally, driving both brand value and pipeline growth.”
On Personalization:
“Customers don’t want just another email—they want relevance, authenticity, and creativity at every touchpoint.”
Highlights from this episode
What inspired you to start Sendoso?
Kris reflected on his early career in software sales and the challenges he encountered with email saturation, even eight years ago. He noticed that traditional channels like email were becoming less effective in capturing buyers’ attention, and customers were increasingly ignoring generic messages. To stand out, Kris started sending handwritten notes, gifts, and swag manually. These personalized touches worked exceptionally well but were time-consuming and inefficient.
Recognizing this gap in the market, Kris envisioned an automated solution to streamline and scale these efforts. This led to the creation of Sendoso, a platform that allows companies to integrate personalized gifting into their sales and marketing strategies. Kris emphasized that the genesis of Sendoso was rooted in solving a real-world problem with a practical, scalable solution.
What is the importance of thought leadership for B2B companies?
Kris explained that thought leadership is essential for B2B companies because it serves three main purposes:
- Educating the Market: Especially in new or emerging categories, buyers need to understand the value of a product or service. Thought leadership helps companies position themselves as experts while educating prospects on how to integrate their offerings into their workflows.
- Inspiring Employees: Thought leadership isn’t just external; it motivates employees to take part in the conversation. Kris shared how his posts inspired colleagues across departments—whether in sales, marketing, or product—to start sharing their own insights, fostering a culture of collaboration and innovation.
- Generating Quality Leads: Buyers today rely heavily on peer recommendations and authentic content rather than direct sales pitches. Thought leadership attracts engaged prospects by addressing their pain points and providing actionable advice, ultimately driving lead generation.
What strategies can companies use to get started with thought leadership?
Kris shared several practical approaches for companies looking to build thought leadership:
- Idea Collection: Maintain a running Google Doc or similar platform where team members can jot down ideas, even as simple “chicken scratch” notes.
- Using AI Tools: Tools like ChatGPT can help refine raw ideas, provide additional perspectives, or create first drafts. AI can also speed up research and validation of content ideas.
- Customer Interviews: Meeting customers, whether casually over coffee or through formal interviews, provides invaluable insights. Listening to customers’ language and understanding their pain points can inspire relevant and impactful content.
- Podcasts as a Forcing Function: Kris pointed out that participating in podcasts like OnBase is a great way to crystallize ideas, think critically, and share them with a broader audience.
How can thought leadership contribute to pipeline growth?
Thought leadership plays a critical role in driving pipeline growth by enabling companies to engage with audiences in meaningful ways. Kris explained:
- Social Media Integration: Sharing thought leadership content, such as LinkedIn posts, videos, or snippets from podcasts, can amplify a company’s reach and influence.
- Recycling Content: Repurpose thought leadership pieces into various formats—such as PS sections in outbound emails or follow-ups from account managers—to keep the messaging consistent and relevant across channels.
- Earning vs. Buying an Audience: Unlike paid media campaigns, which have a temporary impact, thought leadership builds a loyal, organic audience that delivers long-term value and strengthens the brand.
- AI Tools for Snippet Creation: Modern AI tools can help chop up long-form content into bite-sized, engaging pieces, making it easier to distribute and sustain audience interest.
What metrics or strategies can measure the impact of thought leadership?
Measuring thought leadership’s impact is often a mix of direct and indirect metrics. Kris highlighted:
- Trackable Metrics: Use UTM parameters on social media posts and links to track click-through rates and engagement. Monitor spikes in organic and direct website traffic that align with thought leadership campaigns.
- Correlation Analysis: While it’s not always a direct path from a thought leadership post to a sale, Kris’s team looks for correlations between content and other KPIs, such as lead quality or pipeline growth.
- Long-Term Investment: Some benefits, like brand awareness and community engagement, are harder to quantify but have a lasting impact. Kris encouraged leaders to see thought leadership as part of a broader, long-term strategy rather than obsessing over immediate ROI.
What is the biggest challenge in B2B sales today?
Kris identified orchestration as the biggest challenge. With so many tools, data points, and channels available, the difficulty lies in aligning these resources into a seamless, synchronized process. Misalignment between sales, marketing, and operations can lead to inefficiencies, missed opportunities, and inconsistent customer experiences.
Kris emphasized the importance of building systems and processes that integrate tools effectively, ensuring that every team member has the right data and insights at the right time.
What’s your favorite direct mail campaign from Sendoso?
Kris shared his favorite campaign—a Halloween-themed piñata initiative. It combined SDR outreach, trade show promotions, and a dedicated web landing page to create a spooky, interactive experience. Social media posts of recipients unboxing the piñatas generated user-generated content, which was fed back into the campaign for even more visibility. The campaign was a resounding success, generating millions of dollars in pipeline and demonstrating the power of integrated direct mail efforts.
Tech recommendations
- Clay: AI-assisted outbound orchestration
- Hyperbound: AI coaching for sales teams
- Grace: AI-driven account management
- Feeder: A content aggregator
Resource recommendations
Books:
Newsletters:
Shout-outs
- Anthony Kennada, Founder & CEO at AudiencePlus Audience Plus, for his innovative community-building strategies.
- Andy Mewborn, Founder & Customer Support at Distribute, for his thought leadership as a seller-turned-founder.
- Carilu Dietrich, Hypergrowth Advisor, for her insightful newsletter on scaling businesses.
