
Selling the Cloud
Mark Petruzzi, KK Anderson, Paul Melchiorre
Selling the Cloud delves into the stories of C-suite veterans in Sales, Marketing, Customer Success, and RevOps, revealing the secrets behind building successful SaaS empires. Each episode features seasoned leaders who walk through their career journeys, sharing the wins and lessons learned along the way. From mastering customer acquisition to leveraging AI-powered marketing and sales strategies, our guests provide actionable insights for driving growth and business success in the B2B SaaS space.
Guided by a powerhouse team of co-hosts, including Mark Petruzzi, Paul Melchiorre, and Kristin "KK" Anderson, Selling the Cloud offers a front-row seat to the evolving world of Go-To-Market strategies. This podcast extends the insights from the best-selling books "Selling the Cloud" and "Data and Diagnosis-driven Selling", co-authored by Mark Petruzzi and Paul Melchiorre, making it your go-to source for the latest trends and practical tips in SaaS excellence.
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Top 10 Selling the Cloud Episodes
Goodpods has curated a list of the 10 best Selling the Cloud episodes, ranked by the number of listens and likes each episode have garnered from our listeners. If you are listening to Selling the Cloud for the first time, there's no better place to start than with one of these standout episodes. If you are a fan of the show, vote for your favorite Selling the Cloud episode by adding your comments to the episode page.

Inside Sales + Enterprise Buyers - with Sally Duby, Chief Sales Officer at The Bridge Group
Selling the Cloud
09/25/24 • 34 min
Join us as we revisit a classic episode with Sally Duby, the Chief Sales Officer at The Bridge Group and a co-founder of the Silicon Valley VP Sales Forum who brings over 25 years of experience to the evolving world of Inside Sales and business development.
In this episode of Selling the Cloud, we discuss the evolution of Inside Sales in the SaaS/Cloud industry, and specifically how Inside Sales is being used in the pursuit of enterprise-class customers.
Sally first learned the craft of Inside Sales at Oracle, which was the first traditional enterprise software company to prove that inside sales is applicable for enterprise software sales.
Leap forward to 2021 and the path to become an Inside Sales professional often starts in the Sales Development Representative (SDR) role. This role is about learning the outbound lead generation and opportunity qualification process and is the traditional stepping stone to an inside sales role.
Traditionally, Inside Sales ran the full lifecycle of lead to close for SMB or mid-market target buyers, and/or total contract values less than $25K...that dynamic is changing. COVID has accelerated the evolution of the Inside Sales function to more effectively focus on and close enterprise-class deals up to and above $100K ACV. SaaS companies define "Enterprise" target markets by employee size (such as > 10,000 employees) or revenue (such as > $1B).
Chief Revenue Officers are not investing enough time in understanding, valuing, and promoting the Sales Development function as a great starting point for future leaders of the company. In fact, with marketing and sales becoming more integrated, and responsibilities blurred, the skills an SDR develops in gaining buyer engagement and interest before transitioning to sales bodes well for understanding the tactics required for marketing and sales.
Sally highlights why serving in multiple roles across sales and operations is a critical investment that early-career sales professionals can make to pave their road to the Chief Revenue Officer role. Sales Development Rep, sales operations manager, inside sales - commercial, inside sales - enterprise, and even revenue operations or growth marketing are all great roles to build the next generation path to become CRO!
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10/03/24 • 32 min
Join us as we revisit this episode with Gerhard Gschwandtner, the founder of Selling Power Magazine and creator of the Sales 3.0 Conference has been teaching and training sales professionals for 30+ years. His insights on sales success and mindsets are more prevalent today than ever.
On this episode, Gerhard shares his insights based upon his experiences interviewing hundreds of extremely successful business people including Mark Cuban, Bill McDermott (SAP + ServiceNow), Keith Krach (DocuSign + Ariba) and training thousands of B2B Sales professionals.
The B2B Sales profession has been changed dramatically by technology, including the customer/salesperson relationship. Another change is how data impacts the profession, but an even bigger topic impacting sales success may be the "Mindset".
Gerhard shared there are three key components of B2B sales success: 1) Skill Set; 2) Tool Kit; 3) Mindset. The mindset is about how well one is functioning cognitively and emotionally. A key question every B2B Sales professional should ask themselves, "are you Mind Full or mindful?". Developing a positive mindset is an area that individual sales professionals and companies are not investing enough time, energy, or resources.
Another topic we discussed is an emerging and disturbing trend in B2B SaaS/Cloud sales performance. The latest research indicates that less than 60% of B2B Sales professionals achieved quota in 2020. Gerhard highlighted the issue rests primarily on the shoulders of the SaaS company leaders who are not investing enough in on-boarding, training, and coaching of sales professionals.
Gerhard shared an example highlighting the power of having a no-limit, positive mindset. A sales professional attended a positive mindset training session, decided to apply the envisioning, no-limit thinking to his golf game, and in his very next round, hit his first hole in one!
If you are a B2B sales professional or led and/or depend on B2B Sales professionals to drive your company performance, this is a great listen!
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Customer Success, Success - with Eileen Voynick
Selling the Cloud
10/16/24 • 36 min
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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10/30/24 • 28 min
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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11/13/24 • 25 min
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.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

12/18/24 • 46 min
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)
Don’t miss this episode of Selling the Cloud! If you enjoy the conversation, please subscribe and leave us a review.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Getting the VP Sales Hire Right - Right Now - with Amy Volas
Selling the Cloud
10/08/21 • 34 min
The average tenure of a Vice President of Sales in the B2B Cloud industry is reported to be anywhere between 16 - 20 months, with 18 months being the median.
Why is the tenure so short? Is this really an issue considering the high growth rates of B2B Cloud companies? How can we increase the tenure of the VP Sales?
Amy Volas has a broad array of experiences in B2B Technology including roles as enterprise sales professional, recruiter, and sales leadership, and is well-positioned to opine on this critical topic.
B2B Tech sales experiences a 30%+ attrition every year and this was before the trending topic of the Great Resignation!
Missing the VP Sales hire is a seven-figure mistake, and there are basic steps that can be taken to reduce the probability of a poor fit hire.
It starts first with clearly defining the "job" that needs to be done now, and not hiring for the future state 2-3 years down the road. Identifying the "milestone" that you want the VP Sales to help you attain is a great first step. Being real, by clearly defining the "work" that needs to be done NOW is critical to hiring the candidate who has the experience and skill sets to accomplish that goal, but may not be the right person to lead the efforts to the second or third milestone years down the road. In fact, in Amy's 20 years of experience, she has only seen one (1) VP Sales successfully scale from $1M to $1B+.
Just because a VP Sales has been part of a company that scaled to $100M+, that does not necessarily translate to what is needed when a company is just beginning to scale from $1M to $5M. By clearly defining what is needed in the next 12 months, you can develop the criteria, including specific experiences and skills sets, all captured within an associated scorecard for the VP Sales candidates.
Being honest is a top recommendation that Amy says every CEO needs to bring into the VP Sales recruitment process. At $1M ARR, let the candidate know that you are hiring a VP Sales to get to $10M ARR, and that this person may or may not be the VP Sales when the company is trying to scale from $20M to $50M.
This honesty in the VP Sales recruitment process goes both ways, as a candidate who may be a great fit for scaling a company from $20M to $100M+ may not be a good fit for scaling a business from $1M to $10M. An example, if a candidate wants to be a CRO, responsible for marketing, sales, and customer success for a company with less than $1M ARR, they may be a "poor fit" for this stage of the company.
It is imperative to be very careful and precise in this hyper-competitive market. Stepping back and clearly defining the top goals for the VP Sales candidate over the next 12 months is critical to minimizing the risk of over or under-hiring for this critical role.
A key takeaway from this conversation - with a 18-month average tenure for a VP Sales in the B2B Cloud industry may be ok...as long as both the candidate and the hiring executive is honest and transparent about the role, the goals, and the commitment to providing an environment for growth...though it may not be in the top sales executive role.
Amy also highlights the importance of "self-awareness". No one can be great at every aspect of their role, and being able to admit when you need help and then be confident in asking for help. All too often, assumptions between the CEO and VP Sales lead to a lack of credibility and/or trust. As a sales leader, being able to say this is where I need help, here is the result of me getting assistance and this is who I need help from (type of person/resource) and what it will cost.
If you are hiring or interviewing for a VP Sales role in the B2B Tech industry, this conversation with Amy Volas is a great listen!
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04/09/24 • 21 min
Today we are covering three main areas.
1) the strategies that B2B companies can use to alignment strategy across marketing, rev ops, and sales.
2) how data analytics helps marketing, rev ops, and sales work more effectively together.
3) how should we be thinking about continuous improvement across marketing, rev ops, and sales.
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08/29/24 • 36 min
As we near the end of Q3, we thought it would be a great time to re-listen to "Transforming an Enterprise Sales Organization - with Cathy Minter, CRO at R3"
Cathy shares her experiences in taking over the role of the CRO in an early stage pioneer in applying Block Chain to enterprise level application development.
The need for transformation was initially based upon the original formation of R3, which was founded as a consortium of large financial service companies exploring how Block Chain could impact and be leveraged in the banking industry. Initially, R3 was more a consulting company and think tank comprised of investment banking professionals and not an enterprise software platform, with an enterprise sales organization.
Cathy's initial challenge was to build the processes, infrastructure and organization required to evangelize the opportunity that Block Chain provides to application development of the future.
Becoming a "Customer First" company started by getting the executive team aligned on building a customer centric culture that would serve them well over the long haul. It was then translated into the sales process that transitioned from product/feature/function to a solution, business value centric methodology. The use of "Proof of Technology" phase "0" programs to ensure both the business benefit and technical fit was used while embracing a "land and expand" customer acquisition and expansion strategy.
Marketing and Sales alignment was discussed as a key responsibility of a CRO. When marketing and sales became part of the same reporting structure to Cathy at R3, that was when alignment became integration. A critical inflection point happened when marketing made all of their "goals" yet sales and the company missed their revenue goals...it was time to align marketing and sales to the same outcome based goals and integrate the processes, platforms and organizations to the end to end customer buying journey.
Lastly, Cathy shared how to identify enterprise sales candidates for the traits of resilience. In fact, she linked the candidate question "tell me about the last five deals you lost and what did you learn from those" as a way to understand both resilience and a candidates ability to accept responsibility and learn from those experiences.
If you want to become a Chief Revenue officer in an enterprise sales environment, and especially one where the need is to transform the company to a customer first, solution sales methodology, this is a great listen.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Moving beyond Data Driven to Metrics Informed Decisions - with Michael Pollack, CEO Intricately
Selling the Cloud
09/05/24 • 36 min
As the landscape of B2B marketing and sales continues to grow, it's the perfect time to revisit this insightful conversation and Michael Pollack’s perspectives on optimizing your data strategy for more effective customer acquisition.
Moving from data driven to metrics informed decisions and what does this mean for customer acquisition professionals?
This was a primary topic of conversation on the latest Selling the Cloud podcast with Michael Pollack, Intricately CEO
Data is like water - it's really important if you don't have any but what if you have TOO MUCH? Water's value increases exponentially when you process or distill it into higher value outcomes (coffee vs water). This applies to B2B Marketing and Sales by evolving your data strategy from "contacts to context" - creating marketing & sales intelligence
CRM, Martech and Salestech platforms contain and create a lot of content (data) - but not enough context such as:
What to say and/or what content to share
When do you share it and how
How do you say it or how do you message the content
Marketing can add more value to revenue growth by REDUCING the number of leads and moving to a "disqualification" versus "qualification" orientation. Disqualifying low fit leads, contacts, and prospects increases time invested on high quality leads & opportunities
We all know the buying journey has changed - but why are we still using techniques from 10 years ago?
Mike has some interesting insights and ideas that he shares in this episode.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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FAQ
How many episodes does Selling the Cloud have?
Selling the Cloud currently has 77 episodes available.
What topics does Selling the Cloud cover?
The podcast is about Cloud, B2B Sales, Management, Saas, Podcasts, Technology, Sales, Business and B2B.
What is the most popular episode on Selling the Cloud?
The episode title 'Sell without Selling Out - with Andy Paul' is the most popular.
What is the average episode length on Selling the Cloud?
The average episode length on Selling the Cloud is 32 minutes.
How often are episodes of Selling the Cloud released?
Episodes of Selling the Cloud are typically released every 7 days.
When was the first episode of Selling the Cloud?
The first episode of Selling the Cloud was released on Feb 3, 2021.
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