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.

  • 36 minutes 24 seconds
    Role of a Private Equity Operating Partner - with Paul Stansik, Partner ParkerGale Capital

    Private Equity (PE) firms are becoming a larger part of the exit optionality for B2B SaaS Founders and CEOs. Over the past few years, PE firms have gone down the market to evaluate companies in the $5M - $20M ARR range which was traditionally the domain of Venture Capital.

    In today's episode, we cover several aspects of being an Operating Partner at a Private Equity firm with Paul Stansik, Partner at ParkerGale Capital including:

    • The role of an Operating Partner at a PE firm
    • The evolution of an Operating Partner over the past five years
    • How to work with a PE Operating Partner as a GTM executive
    • The most concerning “metrics trends” over the last 12 months
    • What CEOs should expect from their VP of Sales

    Paul started with the four primary roles of an operating partner in PE including: 

    1) Keeper of the standards and having a strong view and sense of what "good" looks like. Documenting the processes and associated measurements that lead to the strongest performance across customer acquisition, retention, and expansion.

    2) Being a strategic diplomat - nothing gets done unless there is an agreement in place as an operating partner does not "OWN" the process so they need to get the management team to a place of agreeing that something needs to be done and then agree to the "WHAT" of needs to be done.

    3) Help to keep score - many founders may not have yet implemented a robust measurement system across the GTM motions. Establishing those measurements provides more insight and predictability of how success is being measured and reported. This includes metrics definitions, instrumentation, and reporting cadence.

    4) Creating an environment and/or culture of the company that includes being supportive, yet demanding to ensure the investment is on track to provide the targeted return on investment.

    What are the current SaaS metrics trends that are most concerning? Paul highlighted that "quota attainment" in the 30% - 50% range is extremely concerning. What makes this level of quota achievement acceptable and what to do about it? If you are a CRO knowing that a low percentage of new reps will make quota and not doing something about it is a real problem. Paul posted an article on LinkedIn on "Why Sales Sucks" and this is the primary theme of the article.

    If you are working with or will be starting to work with an Operating Partner in a Private Equity firm this conversation is chalked full of great insights and ideas.

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    15 May 2024, 12:40 pm
  • 28 minutes 48 seconds
    AI Enabled Customer Communications - with David Daneshgar, Co-Founder and CEO Whippy

    How does being a World Series of Poker champion influence the entrepreneurial journey? That was one of the surprising insights that David Daneshgar, Co-Founder and CEO of Whippy shared during his appearance on this weeks episode.

    During David's conversation with our host, Ray Rike he shared his experiences and vision for AI enabled customer communications which including the below topics:

    • How being a World Series of Poker Champion helps David as an entrepreneur
    • The promise, potential and reality of AI empowered customer communications
    • Customer Use Cases for AI enabled customer communications


    If you are responsible for a company that has a large number of customers, and customer communications this episode provides thought provoking insights into how AI can not only enable but transform how companies interact and engage with their customers.


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    8 May 2024, 3:22 pm
  • 27 minutes 13 seconds
    The Challenges of a Start-Up entering a Mature Market - with Nicolas Kopp, Founder and CEO Rillet

    Nicolas Kopp is the Founder and CEO of Rillet - with the vision to help recurring revenue companies leverage a Financial Management Platform purpose-built for their business model.

    During our conversation with Nic we covered the following topics:

    • Unique Accounting Challenges in a Recurring Revenue Model
    • The Importance of Revenue Recognition in a Recurring Revenue Business
    • Financial Performance Reporting beyond the Income Statement and Balance Sheet
    • Entering a Mature Market Category with a New Product

    One of the first challenges a recurring revenue business will face is translating an annual subscription and the associated "bookings" into GAAP revenue. During Nic's previous roles including working at a recurring revenue that scaled to over $100M AR, he saw the challenges firsthand that Finance had with converting subscription revenue into GAAP revenue.

    What are some of the most common challenges Nic sees in the market?

    • #1 is what is my MRR/ARR and do I trust it
    • What is my deferred revenue
    • Do I trust my accounts receivables report


    Traditional accounting platforms, such as QuickBooks - though solid, functional software is that they do not typically have the concept of "recurring revenue" and the unique revenue management, reporting, and SaaS metrics that are specific to a recurring revenue business.

    One of the primary challenges that Nic and Rillet faced when first launching their product is that the Accounting Platform space is quite mature, and most companies are not proactively looking to swap out their technology until scaling revenue which introduces new challenges and financial management challenges that cannot be addressed with their current platform. This is also often associated with when a first-time VP Finance or senior finance executive enters the picture and quickly realizes they do not have the information or infrastructure required to manage "by the numbers".

    If you are a founder/CEO entering a mature category or a Finance leader who is struggling with Financial Reporting in a Recurring Revenue business - this conversation is full of unique insights and ideas.

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    25 April 2024, 2:28 pm
  • 35 minutes 10 seconds
    Building a Community for B2B Marketers - with Dave Gerhardt, Founder and CEO Exit Five

    Dave Gerhardt, the founder and CEO of Exit Five, former Chief Marketing Officer at Privy, and Chief Brand Officer at Drift discusses the challenges, opportunities, and success strategies for building a Community for B2B Marketers.

    In 2021, Dave started Exit Five as a community for B2B Marketers as a side project while at Privy. it started by posting on LinkedIn and launching a podcast building a following and then creating a community at $10 per month. Within the first 60 days, over 1,000 members joined the community and now the community includes over 3,000 B2B Marketers.

    Dave defines Exit Five as a media company focused on B2B Marketing. With over 3,000 members Dave has a unique perspective on the role of Chief Marketing Officers and their organizations.  

    Over the past 2-3 years, the environment has changed resulting in much greater scrutiny on Marketing expenses and thus rigor has returned. Moreover, the market conditions have forced CMOs to ensure Marketing and Sales are more tightly aligned - especially as Dave Kellogg says if the CEO goes right and the CRO goes left - the best CMOs stay close to the CRO by going left.

    What does Dave think about measuring ROI on evolving trends such as community-led growth or media-led growth? Dave highlighted this is a common problem, and part of the reality is that good marketers just need to know that these are critical "long-term" strategies, that need to be blended with up to 70% of the investments being more short-focused, but having the courage to help the CFO and CEO understand the strategic, long-term value of the other 30% of Marketing investment. Bottom line, getting the CEO and CFO to understand the strategic value of Marketing is a key skill of those most successful CMOs who can see the return over multiple years, not just a few quarters.

    Another point Dave highlighted was that over time members of your community will self-identify how they heard about your solutions and why they decided to "raise their hand" to buy something. Community is even more important when the deals are bigger and the risks are heightened. 

    If you are thinking about or modeling the investment and returns of building a B2B community, this conversation with Dave Gerhardt is full of great ideas and critical insights into what turns an audience into a community.

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    16 April 2024, 8:13 pm
  • 26 minutes 16 seconds
    Original Research as a Content Marketing Asset - with Becky Lawlor, Redpoint Content

    Becky Lawlor is the founder, of Redpoint Content, which advises and assists technology companies by providing original research services and content marketing services

    • Evolution of Content Marketing
    • Role of Research in a Content Marketing Strategy
    • Original Research Content Challenges


    Over the past 3-5 years, content marketing has evolved from a "nice to have" versus a "must have". The primary goals include increasing brand awareness, enhancing demand creation, and ultimately generating pipeline. Over the past 12 - 18 months in an environment of increased efficiency and reduced expenses, the quality of content is trumping content quantity. The benefit of AI is as much about quality as it is about producing more content with fewer resources.

    Becky started by sharing that a good content marketing strategy and even organizational structure begins with understanding what the target audience is looking for and reflects a high level of engagement. Becky's findings are that "original research" is consistently one of the highest-performing content marketing assets, in fact, many of Becky's clients report that original research-based content performs 2x - 3x higher, as measured by downloads" as other types of content, such as how to guides.

    Becky highlighted that while industry analysts provide a valuable service, most technology buyers understand there is a certain "pay to play" aspect to analyst-published research which increases the value of a brand's own "primary research". One key caveat is that when a whitepaper is a "funded project" for a brand - that an analyst report is not that much more valuable than a brand conducting its own "original research".

    If you are responsible or depend on pipeline creation, or have direct responsibility for identifying, creating, and publishing content that increases brand awareness and drives demand creation, this is a great listen!!


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    9 April 2024, 8:58 pm
  • 26 minutes 54 seconds
    Cloud Service Agreement Benchmarks - with Jake Stein, Founder and CEO Common Paper

    Jake Stein, Founder and CEO Common Paper is a multiple time founder of B2B SaaS companies including his third with the goal to help standardize Master Service Agreements across the Cloud industry.

    In today's episode we will be covering three main topics:

    • Vision behind standardizing Cloud Service Agreements
    • Cloud Service Agreement Benchmarks
    • Challenges and Advantages of being a multiple time B2B SaaS founder


    What was the catalyst behind founding Common Paper? Jake highlighted that everything regarding contracts in his previous two start-ups was just too hard! Starting a partnership with the debate and sometimes misalignment that goes with contract negotiation is not consistent to a mutually beneficial partnership. Jake highlighted that when you buy a house - almost every state has a standard real estate purchase agreement. Even the B2B Tech industry has standardized some fund raising agreements, such as the SAFE agreement.

    The first participants are often early stage SaaS companies, who have a strong desire to remove the friction and resources required for new customer agreements. Currently 20,000 different companies have downloaded the standardized agreement, and 1,000+ companies have used the Common Paper platform to sign the standardized agreements with their customers.

    As a by product of having 1,000+ companies using the Common Paper standard Cloud Service Agreement - this provides unique access to the data and metrics associated with all the contracts being signed on their platform. Some of the interesting benchmarks include:

    • 90% of Cloud Service Agreements have an auto renewal clause
    • 29% of Cloud Service Agreements have built in price increases (averaging 5% - 8% per year)
    • 70% of Cloud Service Agreements are annual subscriptions
    • 48% invoice monthly and 40% invoice once annually
    • 85% of Cloud Service Agreements cap "Limitation of Liability" at 1x fees paid in previous 12 months
    • The presence of Data Privacy and AI increased 10x over past 12 months (2.5% to 25%)


    To see the rest of the benchmarks from the Common Paper Cloud Service Agreement click here.

    If you are responsible for writing, negotiating or signing Master Service Agreements with SaaS and Cloud companies, this conversation with Jake is chalked full of hard to find insights and benchmarks for the terms and conditions being used today!


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    2 April 2024, 7:40 pm
  • 34 minutes 34 seconds
    The Next Generation of Customer Success - with Jamie Davidson, Founder and CEO Vitally.io

    Jamie Davidson is a two-time Chief Technology and after his stint as a first Chief Customer Officer decided that Customer Success technology needed a next-generation platform with over 500 customers and funding by A16Z. As a result, Vitally.io was born!

    • Impact of Catalyst and Totango on the Customer Success Technology Industry
    • The Future of Customer Success
    • The Evolution of Customer Success Metrics
    • The Challenges of a Founder in Customer Success Technology


    Recently, two leading players in the Customer Success Platform category, Totango and Catalyst announced their plans to merge. Jamie's perspective is that it could be problematic for category momentum in the short term, but was simply a business decision by two companies that were in no way indicative of the Customer Success platform category as a whole or the Customer Success procession.

    How is Customer Success going to evolve over the next few years? Jamie sees Customer Success becoming more strategic, especially with the help of additional data, insights, and AI. Ultimately, a balance of the existing role as the primary customer relationship manager, while becoming more strategic as the "voice of the customer" to better inform product roadmap, marketing messaging, and new customer sales.

    Customer Success, coupled with better tooling has the potential to materially increase the strategic impact that Customer Success delivers. The evolution of Customer Success technology will move beyond the goal of serving the Customer Success leader and will surface insights and data important to other executive leaders beyond the CS leader, including the other GTM leaders and product leaders.


    If you are leading a Customer Success team, making budget allocation decisions for Customer Success, or are just interested in understanding and helping to determine the future of Customer Success in your company, this conversation with Jamie is a very helpful listen!

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    27 March 2024, 2:57 pm
  • 28 minutes 58 seconds
    The Impact of AI on Customer Communications - with Craig Walker, Founder and CEO Dialpad

    Craig Walker, Founder and CEO of Dialpad has trained their artificial intelligence foundational model using over 6 Billion minutes of customer conversations. If you are interested in how AI is currently and will positively impact the value, efficiency, and effectiveness of customer communications for Sales, Customer Service, and beyond this is a must-listen episode of the Metrics that Measure Up Podcast.

    During this episode, we cover a wide-ranging set of topics on how AI (Artificial Intelligence) and specifically generative AI will transform the productivity and business impact of customer communications including:

    • The importance of large amounts of data in training AI models
    • The future of Customer Service in an AI-empowered environment
    • The potential to materially increase the productivity of a sales process with AI


    What is the difference between "customer intelligence" and "conversational intelligence"? First, customer intelligence is built into the foundation of a company's communications infrastructure - think phone system platform. Because of this, in real time a customer intelligence platform can guide customer service and/or sales reps in real-time to increase the efficacy of every customer interaction. Moreover, any external communication can now be enhanced across every function and every conversation.

    Artificial Intelligence is not new, but generative AI is new with the catalyst of OpenAI and ChatGPT in November 2022. Dialpad has been capturing customer conversations to score performance measurements like customer satisfaction and analyze if the customer was satisfied - all before the emergence of generative AI. Once generative emerged, Dialpad unleased their 15 Data Science PhDs to build their own large language model to better understand every customer conversation and in real-time offer up the appropriate response or next step action!

    Now, think about the opportunities uncovered by taking every minute of your company's customer and prospect communications, and customize the large language model specific to your company, your company terms, product names and every other unique "variable" specific to your business?!

    If you are responsible for customer-facing functions and are interested in better understanding how AI can dramatically increase the efficacy of every customer and/or prospect communication, this conversation with Craig Walker, founder and CEO of Dialpad is full of unique insights, ideas, and recommendations that have been formed from over 6 Billion minutes of customer communications.


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    20 March 2024, 8:13 pm
  • 44 minutes 59 seconds
    Ecosystem-Led Growth - with Bob Moore, Founder and CEO Crossbeam

    Ecosystem-Led Growth is an evolution of Partner-Led Growth and is the vision of Bob Moore, Founder and CEO of Crossbeam and the author of Ecosystem-Led Growth.

    Bob started his tech career as an investor at Insight Partners, and then founded RJ Metrics which was acquired by Magento in 2016, now part of Adobe, and then Bob co-founded Stitch Data which was ultimately acquired by Talend and is now part of Click.

    Crossbeam was founded to unlock the modern platform's architecture and data layer enabling companies to collaborate by making it much easier to share data across multiple partner companies. The catalyst to Bob founding Crossbeam was a $2.6B mistake! That mistake was one Bob made at RJ Metrics where they found and then fell out of product-market fit as evidenced by lower growth. When they analyzed the factor leading to the reduced growth, they identified the emergence of the API economy and how buyers wanted to be able to buy point solutions that were easy to integrate with other point solutions - which was the inspiration to build a product that fully leverages the modern data stack and open API ecosystem.

    What is Ecosystem-Led Growth? It is the ability to leverage a network of partners who can easily share insights with partners who sell complimentary products to the same target buyers. Simple questions like do we have customers or prospects in common, or do you have an active sales cycle going on that we could partner on to build a joint solution for the customer?

    What is the difference between building an "app ecosystem" such as the Salesforce App Exchange and a "partner ecosystem"? It starts with a foundation built upon an open system architecture that enables the sharing of data to collaborate on common target customers, and those companies in the ecosystem are willing to share specific data with partners to make the whole greater than the sum of its parts.

    Why are most B2B SaaS companies still using a traditional direct sales model versus focusing more on partner ecosystems as a primary lead source? The answer starts with the negative reputation of how partnership models were implemented, managed, and operated historically. Partnerships were viewed as encroaching on sales rep opportunities and having a partner damage the reputation of their partners by not adequately communicating the value, feature, and function of their partner's solution.

    Modern Ecosystem-Led growth does not rely upon an army of partnership reps, it leverages the data that already exists in each partnership infrastructure, such as their CRM system. Now, based upon corporate policy, rules, and intercompany workflows, an existing partner can share the relevant data with their partner(s) which will enable that sales rep to have access to data that will make approaching a new potential customer armed with relevant data regarding the tech stack and preferences of a potential customer.

    If you are looking for new ways to increase revenue growth efficiency, decrease customer acquisition costs, and identify "best fit" potential customers by participating in an ecosystem with partners who share those goals and understand the concept of "give to get" this episode is chalked full of ideas, insights and applicable steps to leverage the emerging growth strategy of Ecosystem-Led Growth!

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

    12 March 2024, 1:52 pm
  • 28 minutes 30 seconds
    Data and Diagnosis-Driven Selling - with Mark Petruzzi, Author

    Mark Petruzzi, best-selling author of Selling the Cloud has just released his newest book "Data and Diagnosis-Driven Selling" in collaboration with co-authors Bob Scarperi, Paul Melchiorre, and your host of the Metrics that Measure Up Podcast!

    In this episode, we discuss the primary concepts of the book, and the unique approach to including multiple titans in the B2B technology industry as contributors to the book

    The "Data and Diagnosis-Driven Selling" book covers each stage of the Sales process and how following the process dramatically increases sales productivity and revenue growth efficiency. The process steps and associated chapters discussed include:

    • Ideal Customer Profile - which accounts will buy
    • Buyer Personas - which decision-makers can buy
    • Business Diagnosis - uncovering the value
    • Functional Diagnosis - understanding the wins
    • Solution Design - validating the value
    • Data-Driven Funnel Analytics - the end-to-end view
    • How to Measure a Data and Diagnosis-Driven Selling Process
    • The Predictive and Generative AI power move


    If you are a B2B sales professional, sales team leader, or a senior executive looking for ideas to generate more efficient revenue growth - this conversation and the "Data and Diagnosis-Driven Selling" process and book provide great insights, success stories, and applicable steps to take.

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    6 March 2024, 1:49 pm
  • 30 minutes 32 seconds
    Accelerating Growth in a Cautious Capital Environment - with Hayden Stafford, President and CRO Seismic

    Hayden Stafford is the President and Chief Revenue Officer of Seismic, a leading Sales Enablement Platform. He recently dropped by the Metrics that Measure Up Podcast studio to discuss the state of B2B Sales.

    We covered a wide-ranging list of topics and insights including:

    • The State of B2B Sales
    • Accelerating Growth in an “efficient capital” environment
    • Growth is more than metrics…but metrics matter too
    • Sales Process vs Customer Journey - how do they co-exist


    First, Hayden shared how he has seen B2B Sales evolve over the past 12-18 months. Though the fundamentals of B2B Sales success have not changed, they have become more important. With reduced win rates, longer sales cycles, and more people in the buying process it requires B2B Sales organizations to become more effective and efficient. How to make B2B Sales professionals more effective - a recent McKinsey survey said better preparing sales professionals with better enablement and enhanced sales intelligence.

    Many buyers are looking to "consolidate" their SaaS investments, including RevTech into fewer vendors. A key to helping B2B SaaS salespeople be more efficient, one corporate strategy is to expand the product portfolio to become a "platform" versus a "point solution".

    Common measurements to justify Revenue Technology investments include:

    • Go-to-Market Efficiency
    • Buyer Experience
    • Operational Optimization
    • Time to Market / Agility to Market Changes


    If you are directly responsible for a B2B Sales team or have a B2B Sales team that is primarily responsible for your customer acquisition and/or expansion performance, this conversation is full of great ideas and insights!

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

    27 February 2024, 8:35 pm
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