Selling the Cloud

Management
Technology
Business

CRO
SalesExcellence
SalesEnablement
GetAGS
AccelerantGrowthSolutions
B2BSaaS
Cathy Minter
b2b sales
GTMstrategy
Sales
*GTM
*Data Driven
*AI
Paul Melchiorre
Saas
Mark Petruzzi
benchmarkit
customer acquisition
cloud
b2b

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, Cathy Minter, Paul Melchiorre, Katerina Ostrovsky, 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 book, Selling the Cloud, co-authored by Mark Petruzzi and Paul Melchiorre, making it your go-to source for the latest trends and practical tips in SaaS excellence.

What made Zoom - Zoom with Greg Holmes, former Chief Revenue Officer at Zoom Video

In this inaugural episode of the Selling the Cloud podcast, we were joined Greg Holmes, the Chief Revenue Officer of Zoom Video Communications between 2013 and 2020.

Your hosts of the Selling the Cloud podcast are Mark Petruzzi, Digital Sales Transformation consultant at Accenture and Ray Rike founder and CEO of RevOps Squared, the B2B SaaS KPI Benchmarking Index company.

In this episode, Greg shares how Zoom cultivated a "happiness culture" from the very early days at Zoom. Happiness as a concept was first applied to how Zoom made customers feel, and then to employees. They even anointed a CHO - Chief Happiness Officer.

Eric, the founder of Zoom actually gave every new Zoom employee a copy of the book, Delivering Happiness by Tony Hsieh which created the foundation of the Zoom culture. As Zoom grew beyond a single office, happiness crews were established in every office around the globe to promote and amplify the company culture.

Zoom differentiated their solution by being purpose built for video communications in the collaborative, mobile age to make video communications easier and better from solutions developed for more traditional environments.

Early on, a key role of the Zoom sales organization was to be the "voice of the customer" and ensuring that in the early days of product maturation, customer feedback was constantly shared back to the product group.

Authenticity was a core pillar of the Zoom sales hiring profile from the early days. Many of the interview questions for new sales hires were asking for examples of times when they delivered happiness to their customers. In fact, an early sales person was hired based upon the happiness he delivered to Zoom employees when he was a server at a local restaurant that Zoom employees frequented.

As Zoom scaled, finding the key performance indicators by sales team (Enterprise vs SMB vs Commercial) was key to ensuring every team understand the performance metrics that optimized the probability of success. Zoom's early success was found in the education market, and then they moved on to the SMB marketing (< 1,000 employees) and Enterprise (> 1,000 employees) in the first few years.

Zoom also took at outside-in approach to customer acquisition by beginning with mapping the "buyer journey" and building a sales process that followed the buying process versus trying to force their sales process onto the buyer.

We then touched on the power and importance of "resilience" in being a top sales performer. Greg shared that resilience is built upon life experiences, and that seeking out difficult situations and tough challenges is a great way to build resilience. Similar to asking questions about experience delivering happiness, Greg would always ask about the biggest challenges a candidate had faced in life, and what they learned by encountering and hopefully, overcoming the challenges.

Lastly, Greg discussed the power of being humble, and perfecting the art of praise. The unique take on praise was not only learning how to give praise, but also how to accept praise.

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Transforming an Enterprise Sales Organization - with Cathy Minter, CRO at R3

In this episode of the Selling the Cloud podcast, we are joined by Cathy Minter, Chief Revenue Officer 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.

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Moving beyond Data Driven to Metrics Informed Decisions - with Michael Pollack, CEO Intricately

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.

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The emergence of the Chief Revenue Officer - with Paul Melchiorre, Operating Partner at Stripes

In this episode of Selling the Cloud, we are joined by Paul Melchiorre, legendary Silicon Valley Chief Revenue Officer at leading SaaS companies including Ariba and AnaPlan.

Over thirty years, Paul has had the change to be a part of industry leading, high growth companies beginning with SAP where Paul was an early executive for their entry into the North American market.

Paul then in 1998 joined Ariba, an early market entrant and ultimately the acknowledged leader in indirect procurement automation. Paul experienced a unique journey in early stage, venture backed companies by staying at Ariba for over 15 years, including being the Global Sales, Services and Partner top executive for the majority of that time.

Paul shared why, in the Chief Revenue Officer (CRO) role that being responsible for marketing, sales and customer success is a critical element for success. Several reasons that this is so important is that the customer lifecycle has been changed by the SaaS industry, including the growing importance of existing customer expansion revenue in the evolving "Land and Expand" customer acquisition model.

The growing trend of Product Led Growth (PLG) as a customer acquisition motion will continue to increase the importance of an integrated approach to customer acquisition, retention and expansion. This need for an integrated approach to the customer lifecycle is further highlighted when up to 50% of revenue growth is generated by existing customers.

Paul also shares how investing in himself, including earning his MBA in Finance in the middle of his career journey was critical to being a well rounded, CRO that could build credibility with the CFO.

Paul further explored how PLG also impacts the need for product management to become a more integrated part of the revenue generation team.

Another variable discussed is how the stage of the company impacts both the CRO role and the profile of the CRO. Being able to identify CRO's that have hands-on experience in both early stage, Product Market Fit (PMF) to Minimum Viable Repeatability (MVR) and then from MVR to Minimum Viable Traction (MVT) to true scale is a hard find, but more CRO's like that exist in 2021 than every before.

If you have just become a Chief Revenue Officer or have the aspiration to become a CRO in a SaaS or Cloud company, this is a great listen.

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Storytelling in SaaS Enterprise Sales - with Doug Landis, Emergence Capital Growth Partner

Doug Landis, Growth Partner at Emergence Capital was formerly the Chief Storyteller at Box. Before being the Chief Storyteller at Box, Doug was an executive in the Sales Productivity group at Salesforce.

In this episode of Selling the Cloud, we dive deep into how storytelling has become a critical skill for enterprise-class, B2B sales professionals.

One of Doug's early learnings came directly from paying his dues initially as a quota-carrying sales professional at Oracle. Over those early years, Doug discovered his passion for helping others and sharing the secrets that made him successful as an individual sales contributor with his colleagues, thus the move to sales enablement/productivity at Salesforce.

The journey to becoming the "Chief Storyteller" at Box started with the hiring of a new SVP Sales. As the new executive interviewed sales reps across the company, he quickly identified that Box did not have one common message that they were communicating to the market.

This inconsistently led to the new SVP Sales challenging Doug with the task to replicate and scale his ability to communicate consistently through storytelling to the entire sales organization. One of the key areas Doug first identified was that most customer stories were very "rote", and needed to become more interesting to the target buyer(s).

First, Doug engaged Customer Success to capture the Voice of the Customer, and start the journey to train the sales force how to storytelling by focusing on the customer and their experiences and stories. Secondly, the story could not be the same story that the founder and CEO of Box told, because that was his own story and did not easily translate to being told by Account Executives.

Storytelling is not just for natural storytellers, it can be learned by listening to your environment. But it does take thoughtful practice and needs to be tailored to a relevant story, that resonates with the individual buyer(s) needs.

Improv was highlighted as an interesting format to learn how to put yourself in the persona of the person you are speaking with and make your storytelling more impactful.

Storytelling helps one to learn how to transition from one part of the story to the next. This skill is highly relevant to how a B2B Sales professional can learn to enhance the transition from one slide to the next in their sales presentation or demo.

The discussion evolved into "Getting to WOW" and why storytelling is so relevant to founders and CEOs pitching to investors. A common theme for B2B Sales professionals and founders pitching to investors is about getting to the "why" you or your company are uniquely positioned to help the recipient of the story.

Finally, we discussed the benefit of establishing a "Story Library" by stage, by buyer persona, and even the creation of a "storytelling" coach role in the sales enablement function.

Stories should focus on telling stories that relate to individuals by telling the story about how your solution impacted people (buyer personas) not companies.

In today's extremely noisy and saturated B2B SaaS and Cloud market, making your solution and value stand above all others is critical. Storytelling may just be the best way to differentiate yourself and your solution.

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Inside Sales + Enterprise Buyers??? - with Sally Duby, Chief Sales Officer at The Bridge Group

Sally Duby, the Chief Sales Officer at The Bridge Group and a co-founder of the Silicon Valley VP Sales Forum has seen the evolution of inside sales and business development for 25+ years.

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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Sales 3.0 - The evolution of the B2B Sales Mindset - with Gerhard Gschwandtner

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.

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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Social Selling to Digital Selling to Scaling Pipeline Development - with Jamie Shanks, Founder and CEO Sales for Life

B2B Selling continues to evolve, especially in the context of Cloud solutions.

Jamie Shanks, the founder, and CEO of Sales for Life is a true pioneer in Social Selling. Speaking to Jamie is like drinking a double shot of espresso.

Social media for selling was a discovery that Jamie first identified when he reversed engineer what B2B Sales professionals had been doing in outbound sales for years, and then apply on LinkedIn.

Social Selling was initially developed as an "inbound" sales motion focused on three core principles:
- Building an online brand
- Grow a buyer social network
- Share content 1:1 and 1:many

As social selling evolved to an outbound, account-based motion, the category evolved into "Digital Selling" using multiple channels including social networks, video, and multi-touch, multi-channel sequences.

Most recently, the category has morphed into "Modern Selling", spearheaded by companies like Microsoft and IBM which simply highlights the multi-channel aspect of outbound pipeline generation.

Immediately prior to COVID, digital selling was still an "evangelical" exercise and more time was spend on "why" to invest in Digital Selling versus investing in "how" to deploy digital selling.

Within 30 days of COVID hitting, the conversations shifted to the imperative of how do we ensure our sales organization has the basic skills to reach and engage target buyers digitally. Socially surrounding target accounts and target buyers is key to a successful digital selling program. In fact, Satya Nadella, the CEO of Microsoft said 3 years of Digital Transformation happened in 3 months!

Jamie highlighted that the majority of success begins and ends with the buy-in, governance, and accountability of digital selling by senior and front-line sales management. First, identifying the success metrics for a digital selling program is a critical first step, under the auspice of the "expect what you inspect" mantra.

Leaders need to be enabled first, to understand the evolving coaching moments, and ensure the sales plays reflect the new digital selling motion. Jamie discussed "pipeline coverage ratio growth", which starts with quarterly milestones that drive outcomes in 90-day bursts. Then start to measure progress every quarter, as measured by pipeline coverage ratio, and then close rates.

Time-based, period over period "pipeline coverage ratio" is the number one metric to measure the return on digital selling investment. Close rates and revenue performance are lagging indicators that should be measured, but are not good leading indicators.

When asked about what leading companies have done in regards to Digital Selling over the last 12 months, Jamie mentioned that the top 20% of companies have been very progressive in investing in digital selling transformation. 80% did not aggressively invest in the digital transformation of their sales team and fell behind in both pipeline development and new account sales.

Human Capital migration play is the #1 opportunity to grow pipeline. In fact, over 50% of the new pipeline created in many of Jamie's customers came from this play. Leaders who recently joined a new company are much more prone to invest in new, higher-risk ways of growing pipeline and new customer revenue.

We discussed the pros and cons of asking B2B sellers to build a personal brand versus building their employer's brand. Jamie said it is more important to over-index personal brand building in the target buyer "segment". This will be a candidate evaluation criteria that future, potential employers will use to determine a candidate's value to their company!

Jamie is a great listen for anyone responsible for modern selling in a B2B company!

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Customer Success, Success - with Eileen Voynick

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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You're More Than a Number - with Scott Leese

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.

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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