In this episode of Selling the Cloud, co-hosts Mark Petruzzi and KK Anderson sit down with Kris Rudeegraap, Co-Founder and Co-CEO of Sendoso, to discuss his journey from being a successful sales executive to building the leading sending platform that’s reshaping how businesses connect with prospects and customers.

What You’ll Learn:

• Kris’s Entrepreneurial Journey: From selling mistletoe as a kid to creating Sendoso, Chris shares the pivotal moments that sparked his transition from sales rep to founder.
• Scaling a Business: Learn how Kris and his team bootstrapped their way to $400K ARR, then scaled to $20M and beyond through intentional decisions about pricing, team building, and logistics.
• Leveraging AI and Innovation: Explore how AI and intent data are transforming outbound sales and marketing strategies, and how Sendoso is using technology to drive personalization at scale.
• Leadership and Values: Kris delves into his leadership philosophy, the importance of collaboration, and how his core values—creativity, human connection, and teamwork—shape Sendoso’s culture.
• Work-Life Balance: Find out how Kris prioritizes family, vacations, and personal time while leading a high-growth company.

Key Quotes by Kris Rudeegraap:

• “Your network is your net worth. It’s not just what you know, but who you know.”
• “AI will automate the mundane, freeing up sellers to focus on human-driven tasks that create real connection.”
• “Being a collaborative leader means I work for my team, not the other way around.”

Join us for this insightful conversation packed with actionable advice for sales leaders, entrepreneurs, and anyone navigating the rapidly evolving world of B2B sales and marketing.

Resources Mentioned:

• Sendoso: sendoso.com
• Books: The Sales Acceleration Formula by Mark Roberge, Amp It Up by Frank Slootman
• Tools: Clay (clay.com)

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In this episode of Selling in the Cloud, Mark Petruzzi and KK Anderson are joined by Roee Hartuv, the Revenue Architect and Global Practice Leader at Winning by Design. Together, they explore actionable frameworks and insights for building a sustainable and scalable revenue engine in today’s evolving B2B landscape.

What You’ll Learn in This Episode

1. The Revenue Factory Concept:
2. Discover how the "Revenue Factory" provides a framework for sustainable growth in recurring revenue businesses by applying principles from manufacturing to optimize processes, reduce costs, and ensure customer impact.
3. The Bowtie Go-to-Market Model:
4. Learn how this data-driven model visualizes the entire customer journey—from acquisition to retention and expansion—helping organizations achieve lasting success.
5. Data-First Mindset for Revenue Leaders:
6. Understand why adopting a data-first mindset is critical for modern revenue leaders and how to move away from intuition-based decision-making.
7. Going Beyond Acquisition:
8. Find out why many businesses fail to capitalize on their existing customer base and how focusing on expansion can drive growth more efficiently than traditional acquisition methods.
9. Overcoming Leadership Challenges:
10. Explore strategies for breaking down silos, aligning marketing, sales, and customer success, and building collaborative go-to-market teams.

Key Takeaways

• Revenue Factory Framework: Apply manufacturing principles like quality control, process efficiency, and unit economics to design a scalable revenue engine.
• The Importance of Customer Impact: Whether recurring or reoccurring revenue models, ensuring measurable customer impact is essential for sustained growth.
• The Bowtie Advantage: Move beyond the traditional funnel and track the full customer lifecycle for better retention and expansion.
• Data vs. Gut Feeling: Avoid decision-making based solely on intuition—embrace data-driven strategies to adapt to industry shifts and improve team productivity.

Resources & Mentions

• Winning by Design: Explore their frameworks and methodologies on their website.
• Book Recommendation: The Revenue Factory by Winning by Design.
• Connect with Roee Hartuv on LinkedIn.

About the Guest

Roee Hartuv is a seasoned go-to-market consultant and Revenue Architect at Winning by Design. With a background in sales and strategy, Roee helps companies design efficient, data-driven processes to achieve scalable growth. He has a passion for bringing proven frameworks from other industries to B2B recurring revenue models.

About the Podcast

Selling in the Cloud is your go-to podcast for decoding the art and science of B2B sales in the SaaS industry. Join co-hosts Mark Petruzzi and KK Anderson every week as they explore strategies, insights, and experiences from top thought leaders in sales.

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Join us as we look back at how Alexine's journey from aspiring retail buyer to B2B sales leader shaped her career, inspired the founding of the Women in Sales Club, and sparked important conversations on diversity and inclusion in sales.

Alexine's goal after graduating from Purdue University was to become a retail buyer for a leading retailer, Neiman Marcus. Alexine's first manager within the Neiman Marcus buyer program suggested that Alexine might want to pursue a sales career based upon her performance in retail sales during her initial training program.

In college, sales was not highlighted as a potential career path and was often associated with the negative reputation of a used car salesperson. Alexine took this advice and took a proactive, driven approach to identify and earn an opportunity to join a training program for a B2B SaaS company.

Alexine finds certain innate personality traits have served her well in pursuing a career in sales, starting with being self-motivated and self-critical. Her task orientation and natural love for talking with people are also traits she credited for her sales success.

The catalyst for founding the "Women in Sales Club"? The original goal was just to find other women with who they could share their experiences, gain advice, and connect with other people in their field.

Clubhouse was the platform selected, especially due to the popularity of the platform early in 2021. The forum will expand to new forums including Zoom and live events. Clubhouse was viewed as a lower lift to jumpstart a new community.

When asked about any common themes that have been covered, one was diversity, especially how to attract and retain women on B2B Sales Teams. "Imposter syndrome" has been another topic that has been covered more than once. When asked if "imposter syndrome" really existed, and Alexine there are many interesting reads on this, and that exclusionary activities in the workplace may actually lead directly to this feeling of not belonging.

From the very beginning, Alexine and her co-founder, Gabrielle Blackwell were committed to making the forum inclusive, and that men were just as welcome to join. One of the questions asked was how the leading female voices in the B2B tech industry 1.0 influenced their journey. Alexine highlighted this is not the first and will not be the last forum for women in sales, and that they are simply trying to be as inclusive as possible, and provide a vehicle for learning and self-actualization.

Mark went on to provide his "hot take" that women might actually be better equipped for success in sales than men! Alexine shared her data-driven orientation, and that we have blended many of the cultural norms and personality traits that are assigned based upon gender. Her perspective is that sales is a highly "personalized" profession, and it is the individual's personality traits and goals that are the ultimate predictors of success.

For anyone interested in promoting and being an advocate for diversity, equity, and inclusion across the B2B Tech industry, this is an informational and thought-provoking discussion.

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In this re-released episode of Selling the Cloud, we revisit a valuable conversation with Ben Pastro, who dives into the power of partnerships in B2B tech.

Ben Pastro has a long history in professional services and systems integration in the B2B Tech industry, and has several insights and perspectives on the question of if and how to make partnerships successful for a modern B2B Tech company.

After investing 8 years at Oracle, a founding father of leveraging channel partnerships to accelerate revenue growth. Following Oracle, Ben joined Apps Associates which evolved from a traditional on-premise enterprise software systems integrator to a 100% Cloud based consulting firm focused on Oracle Cloud, AWS and Salesforce. Ultimately, Apps Associates was sold to Private Equity. Ben recently founded Anumetric to help founders and leadership teams at technology centric consulting firms looking to scale and operate more efficiently.

The value of a partnership needs to be viewed on both sides from the partners lens. In fact, having a shared focus on the customer’s business value is the best shared objective. In the world of annual subscription, recurring revenue, maintaining a focus on the on-going business value a customer is receiving is critical to the long term success of the partnership.

Traditionally, enterprise software companies would be more prone to “hand off the customer” relationship to the SI and implementation partner. Today, with the relationship being re-evaluated on an annual basis, the software vendor and the consulting partner are better served with sharing a long term orientation to the partnership and to the shared customer.

Partnerships should not emulate a relay race with a hand-off relationship, rather the partners should collaborate on the both selling process and the project implementation side. Specifically, the implementation partner should help to design the sales process when they will be involved in the customer implementation and ultimate success. The most successful partnerships for consulting firms start with an understanding and strong relationship with the software vendors sales resource(s).

If you are just beginning to evaluate a partnership program for your B2B SaaS or Cloud company, or are a B2B Tech implementation and integration services company, Ben is a great resource who has the experiences and insights to optimize partner programs for both B2B Cloud vendors and their consulting partners.

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Tune in as we revisit this episode, where Bob Scarperi reveals how proactive, data-driven strategies help sales teams target high-value prospects and enhance outbound success.

Data-Driven - a phrase we hear often in the B2B Cloud industry - but often as an output from sales activity versus as a primary input to outbound sales activity.

Bob Scarperi, has built a company that focuses on ensuring the right and complete account and contact data are in the sales resource hands before they being the outreach and lead generation process.

The amount of data available to revenue leaders is very deep and wide, however being able to figure out which data to acquire, deploy and use effectively has never been more complex and thus difficult.

40% of the time, the most junior sales resources, sales development resources are responsible for building and prioritizing the lists they use to conduct sales outreach. Often this results in low probability account being elevated in priority to those most likely to buy?

Why are we doing this to early-career sales professionals? Sources like ZoomInfo, D&B, Lattice Engines provide great data, but most organizations have not built a "playbook" on how sales development and account executives should use the data.

Often, the first step is at the corporate level, building an Ideal Customer Profile (ICP) that defines the highest priority accounts to contact. Unfortunately, far too many companies have not defined the ICP(s) in enough detail that an xDR or AE is confident who they should be prioritizing in their outbound outreach and multi-channel cadences.

Procure a list source that allows sales resources to understand the firmographics of each account in their outreach list, which includes variables including revenue, number of employees, industry, and descriptive details about the company.

Once you have a conversation with the target account, seek to understand their buying mode, decision-making process, etc. Then, develop an "account score" that uses the firmographic and discovery information to highlight the priority of investing more time into that account.

Next, we discussed how intent data can add additional context to the account outreach prioritization process. First, use "technographic" information to see if their existing tech stack is favorable to your solution architecture. Intent data can often provide "false positives" if you do not compliment intent data with firmographic and buyer profile that aligns with your defined ICP and Buyer Persona(s).

Quality of account signal, complete account, and contact (buyer persona) data is the winning combo to optimize and maximize the return on investment for outbound activity.

When selling to larger enterprises, understanding the decision process and the roles of the multiple members on the buying committee, which on average exceeds 10 people. This makes the holy grail of understanding the buying process even more difficult, and yet today, even more critical to the probability of success.

CAUTION: data-driven can lead to data overload. Sales leadership needs to define the specific account information that is critical to make the initial outreach relevant. Identify and define the highest priority leading indicators, such as MQL to SQL conversion rate, SQL to Opportunity conversion, and Opportunity to Close rates. Having too many, or non causal metrics to the ultimate outcomes can lead to data saturation versus metrics-informed decisions.

Each company's environment is unique, so ensure your data driven culture is established, continously evaluated and then used to drive metrics informed decisions while eliminating the noise of too much or irrelevant data!

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Join us as we revisit this impactful episode with Joseph Fung and recognize how much has changed in B2B sales since its original airing – with the shifts introduced by COVID-19 still shaping the industry today.

Joseph is a multi-time founder of B2B SaaS companies, and his experience, frustration and challenge with scaling the sales organization was the catalyst to founding a company, Uvaro, purpose built to train the modern B2B sales professional.

As a trained engineer, Joseph wants to see the data that measures the variables that lead to the highest performing sales organization and sales professional. The patterns Joseph was able to identify within the top performing sales organizations, was easy to capture and the better news, not that hard to replicate.

One of the key challenges Joseph sees is that corporations cannot continuously train new sales hires. Thus the average ramp time can be 6, 8 even 12 months. The impact, quota delivery is dramatically decreased in the first year of employment. The resultant goal - how to train sales professionals not only continuously throughout the year, but even before they are hired in early career roles.

Uvaro teaches and trains students with little to no B2B tech sales experience. Uvaro's median student have a median income of $28,000 coming into training (21st percentile) and exit the training program with on target earnings of $70K and greater (46th quartile).

Less than 2% of colleges have a sales curriculum or a sales major. Joseph highlights "prestige" as a factor in the lack of adoption and introduction of sales majors in college. However, as the Cloud industry marches towards total revenue of $800B+, the industry will need 360,000 additional sales professionals to achieve that level.

CEOs, whose success depends on finding and hiring sales professionals, should be motivated to encourage their local colleges and alma maters to introduce sales curriculum, even a sales major to produce more early career sales professionals.

What are the skills required for the modern B2B sales professional of the future? One significant factor impacting these skills is the evolution of Product-Led Growth as a customer acquisition motion. Joseph views this as a re-allocation of investments from marketing to product, and will not materially affect the need for sales professionals, In fact, the average B2B SaaS companies has twice an many sales professionals as they do engineers, and this trend is not changing.

In a PLG company, sales professionals will need to become an expert in the industry and the business process of their customers, with an increased focus on the business value your product enables.

One additional aspect of the modern sales professional will be the ability to expand and retain existing customers in a recurring revenue model. The core skill required for this - the ability to build and maintain trust based relationships with their customers.

Lastly, Joseph shared that grit and understanding how to leverage a system to your advantage are two key reasons why even classically trained engineers and other technical roles can be leveraged to build a successful sales career.

Joseph is a great listen for anyone considering or just wants to learn about a career in B2B Technology sales.

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Who better to write a book about being a VP Sales in the B2B SaaS industry, than 5x VP Sales and leading LinkedIn sales influencer, Scott Leese. Join us as we revisit this episode to dive back into Scott’s journey, insights, and strategies for navigating the complex role of a VP Sales in the fast-paced world of B2B SaaS.

Scott's primary focus has been to help scale early stage B2B SaaS companies scale from $1M to $20M+. This experience was the catalyst for writing a book that covers the good, the bad and the ugly of being an early stage VP Sales.

Scott's style is to identify an under represented topic, lean into the subject and write a less than 100 page book that both educates and entertains. The title, More Than a Number was selected to ensure that every person who has served, wants to serve or is serving in the role remembers they are much more than the quota number that they carry every month, every quarter, every year. Self worth should not be measured by their productivity as measured by quota achievement.

"Better people, perform better" was a phrase that helped to crystalize that evaluating a VP sales primarily or worse, only by their quota performance highlights the short term, and high risk of approach of allowing one's self to be limited to the number they achieve.

Mental health is a real issue that many sales professionals and leaders face. Being able to compartmentalize your sales performance from your performance as a friend, a spouse, a parent, and as a person is critical to living your life with the "More than a Number" mindset.

You're More Than a Number went beyond the softer side of the message, and provides a framework and playbook for first time VP Sales. Critical elements of being a successful VP Sales such as hiring, sales process documentation, coaching, script development, culture development, relationship building, goal setting, delegation and motivating your team.

The power of delegation is a key ingredient to scaling a successful sales organization. An example is the need to develop the ability to "teach by telling" versus "teach by doing". This is especially relevant when joining a sales call with an AE. Understanding that being able to scale a sales team requires allowing a sales person to learn by doing versus watching you do it, while also building the confidence is a critical part of the VP Sales job.

In fact, Scott said the ultimate goal for a VP Sales is to make themselves "irrelevant" by having an entire team of sales people who can manage the entire sales process, end to end with no involvement from the VP Sales.

If you are currently a first time VP Sales, have a desire to become a VP Sales or have been a VP Sales multiple times, listening to Scott Leese as he shares his VP Sales playbook in context of "You're more than a number" is a great listen and read!

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Join us in our re-release of our episode featuring Eileen Voynick and her deep insights into the evolution of Customer Success in the enterprise software industry, from SAP to the modern Cloud era.

Eileen Voynick has held senior operating roles and board leadership roles at companies including SAP, Oracle, Siebel Systems, All Scripts, Sparta Systems, and Chair of the Board at Jefferson Health.

In this episode, Eileen shares the evolution of Customer Success, both as a function and as a focus in the enterprise software industry.

Eileen's initial foray into Customer Success was formed in part by the large SAP partner ecosystem. At SAP, Customer Success was focused on the business value that a customer can derive from the use of their software. A consistent theme across every software deployment model is that business value and satisfaction have to be understood from the C-Suite all the way down to the individual user.

Customer Experience has always been important in the software industry and has an elevated role in the "Cloud". Eileen highlight that if you look at the switching costs of Cloud deployed versus on-premise are very similar in highly regulated fields such as health care and financial services. "Customer Experience" may have a higher focus today however, that is not primarily due to the deployment model, but rather the evolution of software becoming more common across industries, functions, and processes.

Creating a "Customer Journey Map" which includes every touch from initial touchpoint to full implementation and deployment is a critical task to complete for every Cloud company. This includes ensuring that customer touchpoints are also included post successful deployment to ensure that customer engagement is maintained across every customer stakeholder beyond one to two months before a renewal discussion.

We asked Eileen, "what's next?" in the world of Customer Experience, Product Management becoming more focused on customer experience versus feature/function will become table stakes. Eilleen's example of how a vendor wowed doctors after watching how they performed specific tasks and then came back with a prototype that was met with astonishment by the potential customer.

At the end of the day, customer experience boils down to the "business value" that a software provider delivers to each customer.

When the question "who owns an account after it's closed?" was asked, co-host Ray Rike responded with some benchmarks including, CS now consumes 11% of revenue at the median in B2B Cloud companies. Ray shared that Customer Success should own customer value-based upon user engagement, the value received from using the software but CS should NOT own up-sells, and cross-sells, it should be a "team" approach to ensure customer satisfaction and thus customer retention + growth.

Eileen views the CSM as a great facilitator that orchestrates priorities across their company to ensure customer success. In the "land and expand" model, she shared that having an account management team that works closely with Customer Success to identify, nurture and close up-sells and cross-sells is a preferred model. A caveat is that based upon the maturity of the company, this approach will vary.

The CRO needs to take leadership in establishing a sales-oriented, customer value culture that centers around the customer as job 1. This will go a long way towards building cross-functional alignment.

Lastly, we covered the role of the board of directors in helping companies make the Digital Transformation? Eileen shared that over the last 10 years, her primary role as a board member has centered around product and Go-To-Market strategy which are both core to a successful digital transformation journey. Eileen shared that as a board member, understanding the investor thesis and the company objectives to ensure they are aligned is one of her key responsibilities.

Finally, Eileen shared that being a lifelong learner with strong active listening skills are critical for early career profess.

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