

Metrics that Measure Up
Ray Rike
B2B SaaS and Cloud founders, CEOs, and Go-To-Market operating executives share their journey as they scaled their business from $0M ARR to $100M and beyond. The guests share their insights on measurements of success, performance metrics, and benchmarks they use to guide and inform their decision-making and growth journey.Guests include founders and CEOs of amazing success stories such as LinkedIn, DocuSign, Marketo, Gainsight, Salesforce Commerce Cloud, ringDNA, InsightSquared, Cloudera and Gong. Beyond founders and CEOs, we also speak with leading Venture Capitalists, Go-To-Market executives and industry thought leaders who share their experience and insights into customer acquisition, customer retention, and customer expansion best practices.
Episodes
Mentioned books

Apr 14, 2021 • 31min
How Positioning impacts B2B Tech Revenue Growth - with Bob Wright, Firebrick
During 2020, over 96% of B2B SaaS companies updated their messaging and positioning to counteract the short and long-term impact of the pandemic.Fortunately, there are experts on how to position your messaging and value propositions, including Bob Wright, Managing Partner at Firebrick consulting who has helped over 400 B2B tech companies develop and launch new positioning.The first topic we discussed was why an outside consultant is required when the Chief Marketing Officer is well-positioned to led a messaging initiative. The answer was the expertise developed from conducting positioning with 400 different companies, an experience base that no single CMO can possess.Bob highlighted why any positioning effort must start with the understanding that a cross-functional approach is critical to developing any new messaging platform. At the end of the day, messaging and positioning must be about the buyer, and that the messaging must be about the buyer, not about your product, and its feature/function.Any positioning initiative must include sales and pre-sales consulting, in concert with customer feedback. Customer feedback is critical to gaining validation on the value that the buyer is receiving from your solution. Being a "got to have" versus a "nice to have" is critical to success. One key example is the "digital transformation" inflection point that has opened the door to new, innovative vendors. One key to successful positioning is to ensure you align your value to the buyer's and reality, not to your assumptions.B2B SaaS companies have to run three different businesses today including new customer acquisition, existing customer expansion, and retention. This dynamic requires a "spin" on each of these three revenue-generating motion's messaging. Though the foundation of the story needs to remain consistent, that words will need to resonate with the stated purpose.Positioning must be directly linked to key performance metrics. Short term, it should center on increased revenue growth, higher selling price, and increased win rates. A second measurement is how external influencers, including industry analysts who start to use components of your updated positioning.Positioning needs to be centered on the "buyer", and not industry analysts. Positioning must shift when speaking to the user versus the executive buyer. A short version will resonate best with users/buyers and a longer story is best for analysts and investors.Operationalizing positioning needs to cover sales, marketing, services, support, and product. Having enablement, which includes a certification process that includes sales, services, and customer success is critical. Do not forget to communicate the updated positioning with customers and factor their feedback into enhancements.Once everyone in the company is sick of hearing the new positioning, that is a great indication that it has stuck!Lastly, we discussed a customer's return on positioning investment. This customer deployed a new "business-ready data" message, and within twelve months they increased ASP from $30K average contract value (ACV) to $70K ACV, and even closed eighteen new seven-figure deals in the two years following the updated positioning.We closed with the keys to success which including ensuring creating new positioning is a cross-company process that the CEO owns, not drinking too much of your own kool-aid, and removing overused words like scalable, easy to use, flexible, agility, and collaborative - these words mean nothing anymore and worse are boring!If your messaging and company are not standing out from the crowd, this is a great listen to hear the insights and advice from 400+ positioning programs.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Apr 7, 2021 • 41min
Usage Based Pricing + Chief Monetization Officer - with Chris Mele, CEO Software Pricing Partners
Product Led Growth and Usage-Based Pricing are two of the hottest trends in the B2B SaaS and Cloud industry. Annual subscription pricing has been a hallmark of the financial model for SaaS companies. Lately, the move to Usage-Based pricing has attracted investor demand that is pushing Enterprise Value to Revenue multiples up to 15x-25x. Chris Mele, CEO of Software Pricing Partners discussed the caution around moving too quickly to Usage-Based pricing, and provides advice developed from consulting with hundreds of software and SaaS companies on their monetization strategy....yes monetization goes beyond just pricing!First, Chris highlights that "Consumption-Based Pricing" has been around for decades, and that there is not one model - there are many gradients of usage variables. As an example, pricing based upon the number of locations or even the number of users are examples of consumption-based pricing, so it is critical to understand how the usage variable selected is directly aligned to customer value received.Next, we discussed in greater detail how critical it is to ensure that any usage-based pricing model is carefully evaluated and then validated by the customer as to the value they are receiving from the "pricing variable" that you select. Customer Advisory Boards are one great source of pricing model feedback, specifically as it relates to the value they receive. In fact, these sessions will often uncover value nuggets that you were not aware existed.Chris highlights that when considering a pricing model change, a foundational premise is to do "NO HARM" to your existing customer and revenue base. Even as you test pricing models with existing customer's feedback, ensure they understand that their current pricing will be honored with a grandfather clause IF the new pricing model is deployed.A best practice is to implement new pricing first with either a new product and/or a new target market as not to do any damage to the existing customer base and their revenue.As Product Led Growth models continue to evolve, pricing models will be impacted. Pricing is more than a one-time event, or even a single-dimensional subject, as packaging, product functionality, product roadmap, and go-to-market strategy are all impacted by pricing. This is why Chris is recommending the need for a Chief Monetization Officer, who reports to the CEO. It is their primary responsibility to ensure that all cross-functional impacts and requirements of a monetization strategy, including pricing, are considered and understood prior to any decisions or roll-out of a Usage-Based Pricing strategy.For some companies, the primary responsibility for pricing may reside within Marketing, but in the Product Led Growth economy, Chris recommends that monetization is best positioned within a Chief Product Officers domain if the company decides that a Chief Monetization Officer is not the best path at the present time.If you are considering a Usage-Based Pricing model, this episode is chalked full of insights and perspectives that can only be gained from the depth and breadth of pricing model experiences that someone like Chris Mele possesses.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Mar 30, 2021 • 36min
Measuring the Impact of Sales Enablement - with Elay Cohen, founder and CEO, SalesHood
Imagine being asked by Marc Benioff, founder and CEO of Salesforce to ensure that every member of your sales organization can effectively deliver and communicate the latest presentation and messaging that he had just developed. Then after traveling around the world to execute this directive, Marc informs you that the messaging and presentation has been updated, and you need to do it all over again!Our guest, Elay Cohen founder and CEO of SalesHood experienced that exact situation when he was Vice President of Sales Productivity at Salesforce. His experience as Salesforce was a catalyst to Elay founding a SaaS company focused on using technology to make sales enablement more scalable, automated, and on-going.One of the first topics we discussed was the metrics that should be used to measure the business impact of the Sales Enablement function. Elay highlighted "time to ramp" and "time to productivity", defined as time to first deal and second deal closed, and time to hitting quota as the first metric to measure, followed by win rates, average contract value, and sales cycle length.The conversation highlighted the above sales productivity metrics are leading indicators that directly impact higher level, company metrics such as ARR growth, CAC Payback Period, and other critical, company value-creating metrics that the CEO and CFO track and present to investors and the board.Sales productivity, defined as the percentage of sales professional meeting quota was also discussed. Elay called this as distribution of sales attainment, and this metric is indeed important, but not as a leading indicator of sales performance.Benchmarking current sales productivity metrics is a requisite baseline activity to measure the impact of sales enablement. Then the conversation progressed to whether sales enablement will evolve to revenue enablement or Go-To-Market enablement. Elay highlighted that Sales Enablement is a good place to start the introduction of modern learning techniques, and then the results will encourage other departments to adopt the program.The growing importance of Net Dollar Retention was introduced as a company-level key performance indicator that foretells why Customer Success will become a great next candidate to apply the enablement techniques deployed in sales.We then discussed that enabling sales management is just as critical to individual contributor sales resource enablement. Front line management requires a program that includes coaching, recruiting, interviewing, running forecast calls, and conducting territory reviews. Simply providing a playbook on "what to do" will not work and sales enablement needs to sit down and coach alongside the manager to ensure they benefit from feedback from coaching.If increasing customer acquisition and customer expansion performance and productivity is an opportunity you are interested in learning more about, this is a great episode for you.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Mar 23, 2021 • 34min
Lessons Learned from being a 6x SaaS VP Sales - with Scott Leese
Experience is the best teacher. In this episode of the Metrics that Measure Up with Scott Leese we take a deep dive into how experience has informed his career journey.Scott has over twenty years of experience as a six time SaaS VP of Sales, and most amazingly, his average tenure for each role was greater than 3 years in a role that typically experiences a 14-18 month tenure. Scott shares some of his lessons learned and secrets to his sustained success.First, Scott highlighted how critical a Sales Operations leader is to become the foundation of success. Secondly, Scott talked about his own journey to learning how to hire better candidates which has a material impact on a VP Sales ability to be successful in early stage SaaS companies.Next we talked about the important of "sales process" and why Scott says he would even design and implement a structured sales process even before he would hire the first sales resource. Scott says one of the most common mistakes founders make is not to document the sales process that got them the first few deals, and provides insights into the initial scaling of the sales organization.Stage appropriate VP Sales is a common topic and discussion amongst investors, founders, CEO's and even VP's of Sales. Scott's recommendation is to ensure that you design your VP of Sales career journey to embrace and experience every stage of growth. Scott loved the role of being an early stage of VP Sales at SaaS companies, but did find that bias was created that certain "VP Sales" profiles get labeled as only an early stage VP Sales. This discussion led to why stock option programs that are historically based upon time - 4 years is the standard but should be aligned to size/growth accomplishments to reward achieving the goal versus a time horizon that is seldom achieved by the VP Sales in early stage SaaS companies. The other option discussed was to agree on a one-time bonus based upon hitting a pre-defined revenue level, such as $25M or $50M.Scott has leveraged his 20+ years of VP Sales experience to launch his own his own VP Sales consultancy, writing two books including "Rep to Sales Manager", a quickly growing, weekly Thursday Night Sales event, the Surf and Sales event and most recently his own private patreon. Scott highlighted that he built his network and the foundational elements of his entrepreneur journey while he was a full time, VP Sales.Scott also shared how his side hustles, including real estate, his books proceeds and even hold the initial Surf and Sales event during his annual two weeks of PTO. One caveat was ENSURE you are hitting your quota and goals before even considering taking this approach. During the episode we created the concept of "micro-entrepreneurship" which is an interesting step by step approach to moving from employee to entrepreneur.Lastly, Scott discussed that his initial catalyst to building his LinkedIn following was trying to save money on sales rep recruiting. As a result, not only did Scott eliminate the majority of his recruiting costs, he quickly saw the secondary benefit of building his LinkedIn following. He supplement his outreach with content that he thought sales professionals were in desperate need to see, read and learn from and not be charged for this type of educational content.If you love the world of B2B Sales, and are considering creating your own company some day, 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.

Mar 16, 2021 • 32min
Global SaaS Start-Up Community Growth - with Alex Theuma, SaaStock
In this episode of the Metrics that Measure Up podcast, we speak with Alex Theuma, the founder and CEO of SaaStock and the SaaS Revolution podcast.Alex started his career as an enterprise sales professional, and identified his passion for SaaS as he started to write a blog on all things SaaS, called SaaScribe. SaaScribe quickly morphed into a community blog, and enabled Alex to build deep and broad connections across the SaaS ecosystem.Based upon the community of SaaS entrepreneurs that developed, Alex identified the opportunity to launch a European SaaS event. Even though Alex was preparing to be a first time father in three months, Alex jumped head first into launching SaaStock and the first event in 2016 included 700 attendees from over 34 countries.Alex's initial vision behind SaaStock remains consistent to today - to help SaaS founders grow and find success in their SaaS based entrepreneurial venture. The SaaStock Mission is to make a real difference to those participating in the SaaS industry across the world. Being global was not part of the initial vision, as SaaStock was started to focus on SaaS founders across Europe. However, the first SaaStock event in Dublin attracted attendees from 34 different countries. With that as the backdrop, SaaStock expanded quickly to be the first global events company for SaaS founders with events in multiple countries around the world. As the event began to grow, Alex started to partner with communities, initially in Brazil to develop a global footprint. In fact, SaaStock started their global expansion by partnering the Brazil SaaS Forum and now has expanded to SaaStock LATAM. Then, Alex expanded into Asia-Pacific. One material finding was that most SaaS companies in Asia-Pacific need to think globally early on to have a meaningful Target Addressable Market. With the largest SaaS event competitor being headquartered in Silicon Valley, SaaStock initial decided to enter the US market with conferences in New York. Then in 2019 they identified the opportunity to hold an event in downtown San Francisco.2020 brought the reality of needing to pivot from in-person events to virtual events, and was the catalyst for SaaStock Remote. True to their global vision, SaaStock remote could not be conducted just in the 8AM - 5PM US time. So, they pulled the time forward to start at noon in Europe to 10PM in Europe, allowing for European and US SaaS entrepreneurs all to attend. SaaStock Remote LATAM and SaaStock Remote APAC are being held as focused, dedicated virtual events for those specific geographies.Even though 2020 was a down economic period due to the impact of COVID, the SaaS economy continued to thrive. Much like the larger, public SaaS companies, after an initial reaction to cut expenses in March, SaaS start-ups started to quickly emerge into hyper growth in 2H20. Hopin is an example of a European SaaS company that experienced hyper growth, which grew to a $2B valuation within 18 months of launching!When I asked Alex which area of the world he saw the fasted growing for SaaS companies, he first answered that the SaaS world is becoming much flatter, and that San Francisco is not longer the only place to start a SaaS company. Alex did highlight Latin America as a force to be considered for great SaaS unicorns over the next few years.If your goal is be a global SaaS company, 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.

Mar 1, 2021 • 39min
Revenue Intelligence + Advanced Sales Math - with Todd Abbott, InsightSquared CEO
In this episode, we discuss the revolutionary concepts of Revenue Intelligence and Advanced Sales Math with Todd Abbott, CEO at InsightSquared.Revenue Intelligence and Advanced Sales Math are critical competencies to successfully maneuver in todays B2B SaaS reality of compressed sales cycle and the changing customer buying journey.The good news - traditional metrics including lead conversion rates, close rates, pipeline coverage ratio, and sales rep productivity still are helpful to calculate basic sales math. Basic sales math is essentially what level of “X” inputs are required to achieve “Y” outcomes. X being primarily marketing + sales investments and Y being new revenue.Advanced Sales Math takes this concept to another level, and will dramatically increase the performance of the #1 reason why B2B SaaS CRO’s and VP Sales lifespan is less than 18 months. The #1 reason the average CRO / VP Sales tenure is so short - the inherent challenges and low performance of FORECASTING!Research highlights that only 54% of opportunities forecasted to close actually close in the original “closing” accounting period. The average number of times an opportunity “pushes” or changes forecasted close data is 3+ time.A key, new variable in advanced sales math is the ability to factor in buyer engagement metrics, across each step of the buying process across every resource at both the buyer and the seller. The challenge of traditional “event” based sales processes and forecasting were dependent upon the accuracy and timeliness of data in CRM systemsThe proliferation of point solution in martech and salestech has led to even more complexity of filtering through the noise to find the right signals to increase forecast accuracy. Having integrated Go-To-Market teams coupled with an integrated and unified GTM data source is mandatory to enhance revenue intelligence leading to improved forecast performanceThe concepts covered in this episode of Metrics that Measure Up are thought provoking, and even possibly career preserving for any CEO, CFO and CRO in todays B2B SaaS ecosystem.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Feb 23, 2021 • 40min
Getting to WOW - Secrets of Pitching to VCs - with Bill Reichert, Garage Technology Ventures and Pegasus Tech Ventures
If you are contemplating VC funding, this episode of the Metrics that Measure Up podcast is like receiving a master's degree in pitching to VCs from Bill Reichert and his book "Getting to Wow"Key concepts covered include: Ensure your pitch follows the three C's- Clear- Compelling- CredibleCLEAR is removing the complexityDo not fall into the "experts curse" - only you have the depth of expertise on the topic- Ensure anyone can understand what you do in 1-2 sentences- Test your message with fresh brains before your pitch to VCsCOMPELLING - Investors are human - they invest with their "heart" - not just their "head"Ensure your pitch invokes emotional engagement- Go beyond the facts and use short stories ofhow customers are being positively impacted- Imagine if..."CREDIBLE - phrases like "disrupt the entire health care industry" or "we can capture 10% of the market and have $1B in revenue" - can negatively impact your credibility- real life customer stories and proof points go much fartherPITCH DECK - their is no template that fits every pitch but a common theme is - LESS slides is much better (15 or fewer)STORY TELLING - Do not use a single story arc or start with a personal story that led to your creation-use small stories to highlight key pointsEnsure you highlight the SPEED and EFFICIENCY of your Customer Acquisition to highlight your customer acquisition process is repeatable and scalable. Key metrics go beyond just sales cycle length and customer acquisition cost, but also efficiency metrics like Customer Lifetime Value to CAC ratio and your gross margin.Getting to WOW is based upon observing and participating in thousands of entrepreneur pitches to VC's and has been distilled into a guide for any first time or even experienced founder evaluating VC funding.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Feb 23, 2021 • 36min
Selling your Company to Salesforce - with Mike Micucci, former Salesforce Commerce Cloud, CEO
Imagine the experiences gained and lessons learned from founding your own SaaS company, selling it to Saleforce and then becoming the CEO of a Salesforce Business Unit.That was the journey Mike Micucci, who recently left Salesforce eleven years after selling his start-up to Salesforce in 2009 and ultimately rose through the ranks to be the CEO of the Commerce Cloud business.Mike shares the story behind founding GroupSwim, an early B2B collaboration platform that became the foundation for Salesforce Chatter. Then Mike shares the story behind how community cloud and commerce cloud came together, with both a B2B and B2C - or even a B2B2C offering. Over the last 10 years, Commerce Cloud has grown to be over a $1B business and you can rest assured that Metrics were at the heart of most of Mike's strategic decisions.Mike's experiences started when I first met Mike in the initial "vortex" of B2B eCommerce in 1997 - 2001 where he was an integral part of the product management senior leadership teams at Netscape and Commerce One. Then in 2005 he founded GroupSwim, and had firmly established Product Market Fit by the beginning of 2009 when he received two different offers to purchase GroupSwim.Following the GroupSwim acquisition, Mike decided to accept the opportunity to be part of the Corporate Social Network initiative within Salesforce - yes Chatter which launched in 2010. From that experience, Mike pitched the concept of "Community Cloud" to Marc Benioff and Parker Harris. The vision was to build a solution to connect the different "communities" within Salesforce to other communities and companies.By 2020, Community Cloud had reached 650 million users. Interesting that Community Cloud is measured by usage, growth and how much revenue they influence on the other core clouds. Mike shares the Salesforce relentless focus on customer input and feedback into the product lifecycle, especially through the use of Customer Advisory Boards (CAB's) which provides a primary to the product roadmap. In fact, the concept of Commerce Cloud was originally stimulated by a customer who had built their own commerce capability into Community Cloud in 2014.Later in 2014 Salesforce launched Commerce Cloud at Dreamforce. By 2016 Community Cloud and Commerce Cloud became one Salesforce Cloud business unit. Mike share how Digital Commerce grew more in 2020 then in the past few years combined. When COVID first hit, Mike saw his dashboards showing how volume on Commerce Cloud spiked starting in March. Finally, Mike shared he segments metrics into usage metrics and operational metrics. Operational metrics on commerce starts with GMV (Gross Merchandise Value) which hit over $50B GMV in 2020. DAU/MAU (Daily Average Users/Monthly Average Users) was a key metric used to evaluate the health of his business unit. ACV (Annual Contract Value), AOV (Average Order Value) and churn was also tracked daily as key operational metrics. Mike also shares why "branding" and "pricing" are the two hardest aspects of building a Cloud business. In fact, he went into detail on the benefit of a blended pricing model that uses both a subscription model plus usage based pricing levers. One of the hardest parts of a variable usage based pricing model is how best to forecast variable revenue.Mike's story reflects the opportunity, reality and journey that so many corporate leaders in the Cloud have experienced over the last 20+ years. If you are looking for inspiration coupled with detailed insights into how an entrepreneur's journey can evolve from the corporate world to being a founder and then on to the CEO of a $1B+ cloud business, 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.

Feb 16, 2021 • 22min
Breaking Barriers in B2B Sales - with Gidget Pugh, Socially Focused
Breaking into B2B Sales, especially Enterprise level B2B sales is still a challenge for many in todays Cloud and SaaS industry. Even more difficult for those who do not have relevant experience, ore connections and thus the access and opportunity that comes with many forms of inherent privilege.Gidget Pugh broke through those barriers, not in 2021 but beginning in 1998 with the power of self-confidence, drive and often the most important stimulus of all - a compelling reason to bet on yourself.In this episode of the Metrics that Measure Up, we speak with Gidget Pugh a 20+ year veteran in B2B sales who has recently transitioned into founding and launching her own social media agency focused on the community that she is so passionate about - small business - starting in the town that made Gidget who she is - Oakland, California.Gidget shares her journey from mortician - yes a mortician to her first role in B2B Sales at QRS. QRS was the world's largest subscription platform for sharing UPC codes in their product catalogue across the retail industry supply chain in 1998. Then she leverage that experience to working at household technology brand names including Oracle and Facebook.One of the main topics we discussed was how Gidget maneuvered within an industry and companies where often she was the only female, African American in the sales organization if not in the entire company. A recurring theme of "self-confidence" and "color blindness" were critical to her in every environment she entered.We then move on to her decision to leave the corporate world to launch her own social media agency, Socially Focused to help small and medium size businesses to harness the power of social media and on-line engagement building to counter the impact of COVID on their physical presence business and prepare them for the world of digital commerce that has been accelerated by the experiences and resultant digital transformations of every industry.This is an amazing story of drive, determination and self-confidence that provides everyone looking to move beyond the environment of their current state into the future of opportunity a great story of inspiration and reality all in one.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Feb 8, 2021 • 28min
Building your Network versus Networking - in Silicon Valley and Beyond with M.R. Rangaswami
M.R. Rangaswami is an enterprise software executive, angel investor, entrepreneur, corporate eco-strategy expert, community builder, and philanthropist. Wow, is right as his accomplishments are admirable. M.R., as he is known across the software and Cloud/SaaS industry, and around the globe founded the Sandhill Group and sandhill.com in 1997. In fact, the Wall Street Journal placed MR on their front page to highlight his early commitment and success as a leading angel investor in the early days of the Enterprise software movement in Silicon Valley. With over forty years in Silicon Valley, M.R. is probably the most networked person in the industry, through his experiences and connections from founding the Enterprise Software Conference, the Enterprise Retreat for the top SaaS CEOs, the Eco-Forum which is a membership only community of the top 100 executives responsible for driving sustainable green initiatives in Fortune 500 companies, and most recently, Indiaspora to transform the success of Indian American's into meaningful impact worldwide.In this episode, MR discusses the secrets to building his network in Silicon Valley and beyond. He highlights the importance of understanding the difference in building your network versus networking. A key attribute to building a strong, lasting network is to have no expectations beyond helping those in your professional network. Don't sell, don's solicit business, just identify how you can help each person in your network and watch the dividends pay back over the long term.MR and I cover the evolution of the Enterprise software industy to the Enterprise Cloud/SaaS market, the impact that leading cloud and technology companies are having on energy efficiency and green initiatives. If you are a fan of the Silicon Valley experience, and curious to understand how one of the industry's best and most well respected connectors has built his network and reputation, this is a must listen.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.


