Selling the Cloud

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.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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.

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!

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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!

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

We're revisiting this insightful episode as B2B selling continues to evolve, especially within the fast-paced world 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!

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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!

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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!

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

As we revisit this episode, Doug Landis' insights on storytelling in B2B sales are more important than ever. Learn how compelling stories can help differentiate and elevate your message in a crowded market.

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. 

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.