Ray Rike

AI to ROI

Business EN ↓ 247 episodes

AI to ROI is a podcast that shares how enterprises translate AI investments into measurable business value. Hosted by Ray Rike, Founder and CEO of Benchmarkit, the show features senior enterprise leaders and AI software executives who share how AI initiatives move from pilots to production, and how ROI is actually measured and achieved. In addition, each week, we publish a bonus episode with AI to ROI Newsletter co-author, Peter Buchanan to discuss the Big Story of the Week. The AI to ROI podcast is the evolution of the original "Metrics to Measure Up" podcast.

Author

Ray Rike

Category

Business

Podcast website

art19.com

Latest episode

Jul 7, 2026

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Episodes

Customer-In Revenue Operations - with Alison Elworthy, EVP Revenue Operations - HubSpot 09.06.2021

Marketing Operations to Sales Operations to a VP, Customer Success.  This carer path serves as an amazing foundation for a Revenue Operations executive. This is exactly the career path that Alison Elworthy, EVP of Revenue Operations at HubSpot. Alison's experience as a customer success executive was an eye-opening experience for a career-long operations professional who had not previously inv...

Product-Led Growth - Evolution or Revolution - with Wes Bush, ProductLed 01.06.2021

On this episode of the Metrics that Measure Up podcast we are joined by Wes Bush, founder and CEO  of ProductLed. Wes's journey to founding ProductLed and becoming a leading voice on Product-Led Growth started when he was responsible for demand generation for B2B SaaS companies.  Specifically, when he led demand generation at Vidyard, they launched a new product that allowed them to evolve fr...

Product Analytics + Product Led Growth = A Partnership for Success - with Ken Fine, CEO Heap Analytics 25.05.2021

Product Analytics + Product Led Growth are critical partners for success. Ken Fine, CEO of Heap Analytics recently joined me on the Metrics that Measure Up podcast to discuss the inextricable linkage between these two concepts. PLG currently exists in a continuum of maturity, with some companies managing the entire customer lifecycle using a product-led motion, while the majority still using a tra...

Product Led Growth Metrics and Benchmarks - with Sam Richard, OpenView Partners 19.05.2021

Sam Crowell Richard is responsible for growth across the OpenView Partners portfolio. OpenView Partners is a leader in advocating Product Led Growth strategies across their portfolio, which includes leading PLG companies including Calendly. Sam has invested in her career preparing for a growth role in a PLG focused venture capital firm, including learning the secrets of digital marketing in a digi...

B2B SaaS Metrics Evolution and Usage - with Clayton Whitfield, Founder SaaSOptics 12.05.2021

Clayton Whitfield founded SaaSOptics to provide B2B SaaS founders and operators a platform that made it easier to capture, calculate and make better metrics informed decisions. Clayton shared that the core metrics that form the foundation of B2B SaaS company value have not evolved significantly over the 12 years since he founded SaaSOptics, but the understanding and comfort with the metrics have e...

Usage-Based Pricing in B2B SaaS - Trendy Topic or Strategic Value Lever - with Adam Howatson, CEO LogiSense 05.05.2021

Usage-Based Pricing is all the rage across multiple B2B SaaS news outlets.  Subscription-based pricing has been the standard pricing model for over 20 years, which has provided B2B SaaS companies more predictable revenue growth over time versus the famous end of quarter "hockey stick" of perpetual licensing software companies. However, companies such as Twilio, Snowflake and DataDog have...

B2B SaaS Metrics with the Master - Dave Kellogg @kellblog 26.04.2021

B2B SaaS Metrics are talked about in board meetings, investor diligence, executive team meetings, and recently across every corner of the internet from industry influencers and thought leaders. As the host of the Metrics that Measure Up, I was thrilled that I could speak with Dave Kellogg, one of my long-term follows, and a master of all things B2B SaaS metrics. Dave is a multiple-time, CEO and Ch...

Podcasts + MarTech Metrics that Matter - with Ben Shapiro, Host of the MarTech Podcast 20.04.2021

Benjamin Shapiro started his internet marketing career at eBay, one of the first, largest and most data-driven marketplaces in the world.  Ben's 7 years at eBay provided him the foundation of being a great digital marketer, including SEO and content marketing. Ben caught the Silicon Valley start-up bug, and spent the next 8 years in marketing leadership at B2C early-stage companies, and then...

How Positioning impacts B2B Tech Revenue Growth - with Bob Wright, Firebrick 14.04.2021

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 dis...

Usage Based Pricing + Chief Monetization Officer - with Chris Mele, CEO Software Pricing Partners 07.04.2021

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...

Measuring the Impact of Sales Enablement - with Elay Cohen, founder and CEO, SalesHood 30.03.2021

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 agai...

Lessons Learned from being a 6x SaaS VP Sales - with Scott Leese 23.03.2021

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 o...

Global SaaS Start-Up Community Growth - with Alex Theuma, SaaStock 16.03.2021

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 br...

Revenue Intelligence + Advanced Sales Math - with Todd Abbott, InsightSquared CEO 01.03.2021

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 rat...

Getting to WOW - Secrets of Pitching to VCs - with Bill Reichert, Garage Technology Ventures and Pegasus Tech Ventures 23.02.2021

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 - Credible CLEAR is removing the complexity Do not fall into the "experts curse" - on...

Selling your Company to Salesforce - with Mike Micucci, former Salesforce Commerce Cloud, CEO 23.02.2021

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 stor...

Breaking Barriers in B2B Sales - with Gidget Pugh, Socially Focused 16.02.2021

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-co...

Building your Network versus Networking - in Silicon Valley and Beyond with M.R. Rangaswami 08.02.2021

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 thei...

B2B SaaS Metrics that Matter to Growth Stage VCs - with Doug Landis, Emergence Capital 02.02.2021

If you are responsible for driving revenue growth at a SaaS company that is preparing to raise Series A or Series B funding, what are the key metrics investors will expect you to know cold? That is exactly what Doug Landis,  Growth Partner at Emergence Capital shares on this episode of the Metrics that Measure Up podcast. Doug's journey to becoming Growth Partner at Emergence Capital, the fir...

B2B SaaS Finance and Metrics - A European Perspective - with Joyce Mackenzie Liu, Pegafund 19.01.2021

As businesses shift towards the Cloud, SaaS has become the de facto distribution method for modern day software solutions across the US and increasingly so in Europe.  Joyce Mackenzie Liu, Founder of Pegafund which provides go-to market strategy and financial planning services to early stage, high growth B2B SaaS companies shares her perspective on the European ecosystem. In this episode, Joy...

The Wayback Machine + Internet Archive with Brewster Kahle - Founder and Chief Librarian 19.01.2021

Have you ever thought it would be cool to see a website from 5 years ago, 10 years ago, even 20 years ago? That is exactly the vision that Brewster Kahle, founder of the Internet Archive and The Wayback Machine first started to develop in the late 1990's! In fact, Brewster was developing the Wayback Machine simultaneously to running Alexa Internet, one of the first internet browser plug-ins t...

Strategic Acquisition or IPO? - with Tom Reilly - Former CEO, Cloudera and ArcSight 12.01.2021

The most interesting dilemma for a CEO?  The decision that comes with having the option to go public or accept a strategic acquisition offer. Tom Reilly, former CEO at Cloudera has been a CEO with the experience of selling a company to IBM, another company to HP and then taking Cloudera public after raising $766.5M from strategic partner, Intel. Tom says a CEO should invest 20% - 30% of their time...

LinkedIn Co-founder Konstantin Guericke - The keys to building a long lasting B2B Network 05.01.2021

B2B Communities caught fire in 2020 - especially B2B sales communities.  Revenue Collective, Sales Hacker, Modern Sales Pros, RevGenuis, and Bravado all dramatically increased their membership and levels of engagement following the onset of COVID. Who better to discuss the trend of B2B communities, than a founder of the world's largest B2B network, LinkedIn.  Konstantin shares the key differe...

An Entrepreneur's Inner Voice of Doubt - with Mike Smerklo, Next Coast Ventures and Mr. Monkey and Me author 29.12.2020

Mike Smerklo is by any measure a story of entrepreneurial success.   Mike founded a search fund which led to the early stage acquisition of ServiceSource, and he took it to over $300M in revenue,  took the company public, and was the CEO for over 13 years. Then Mike followed his passion to help fellow entrepreneurs and founded Next Coast Ventures in Austin, Texas long before Austin was being heral...

Selling the Cloud - Part 2 with Paul Melchiorre and Mark Petruzzi 23.12.2020

In this episode, we continue the discussion with the authors of Selling the Cloud. Building upon the first half of our conversation where we discussed the need for grit and passion to be success full in Enterprise sales, we move into several new topics.  The Power of No is a key skill to develop.  A great enterprise sales professional is qualifying prospects out every step of the process to reduce...

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