Top Insights From the Best

Top Insights for CEOs, Sales & Marketing Leaders and Investors
from the best experts in the world.

 

Speakers

Don Addington

Chief Revenue Officer at Tackle.io

Don has spent the past 20 years helping individuals and organizations adapt to massive changes in the IT industry – most recently having led the sales teams responsible for Digital Transformation at Pivotal. 

Now, At Tackle, Don and team are helping software companies transform the way they sell.


Max Altschuler

SVP at Outreach.io, Founder of the Sales Hacker Community, Investor

Max Altschuler is the founder and CEO of Sales Hacker, the leading community for the next generation of sales professionals. 

He’s the author of:

  • Sales Engagement: How The World's Fastest Growing Companies are Modernizing Sales Through Humanization at Scale
  • Hacking Sales: The Playbook for Building a High-Velocity Sales Machine
  • Career Hacking for Millennials: How I Built A Career My Way, And How You Can Too

Hacking Sales, Sales Engagement, and Career Hacking For Millennials. A widely recognized thought leader on sales and technology, Max has been published by the Harvard Business Review, Forbes, Money, and more. He was named a top sales expert by both Salesforce and Inc. He keynotes conferences globally and is an investor and advisor for rapid growth startups.

In this episode:

  • How Max built Sales Hacker to 175,000 members
  • The #1 thing that is responsible for making the biggest difference in building a successful company like Outreach.io and the Sales Hacker community
  • Secret 1 from Outreach.io sales floor - the "Boom Email"
  • Secret 2 from Outreach.io sales floor - the "LinkedIn Takeover"
  • Secret 3 from Outreach.io sales floor - the full-time Sequence Content Expert who runs A/B split tests and experiments to generate the best conversions from outbound emails
  • What Bill Gates' "Tech is a magnifying glass" and how it relates to everyone using sales engagement platforms like Outreach
  • What SaaS companies' SDRs can do when everyone around you is also using sales engagement platforms and everyone can send 100's of emails per day - how do you stand out and deliver results
  • Why benchmarks for Outbound SDRs like Meetings Scheduled are not as prevalent / available
  • Why most Outobund SDRs generate 8-15 meetings per month with only top 1% generating 20 and above

Trish Bertuzzi

CEO, The Bridge Group, Book Author, Leading Sales & SDR Expert

Trish Bertuzzi is the founder of The Bridge Group, where she's been helping B2B technology companies build world-class inside sales teams since 1998. Over that time she has promoted inside sales as a community, a profession, and an engine for revenue growth.

In the process, The Bridge Group has worked with over 400 B2B technology clients to drive scalable growth with SDR, AE, and CSM efforts. Trish often remarks how lucky she is to work with an amazing team at The Bridge Group, helping sales and marketing leaders make the big decisions: on models, motions, metrics, and supporting technology.


Adam Boushie

Chief Revenue Officer at Gloo

Adam Boushie leads Gloo’s Sales, Marketing, Success, Support, Business Systems and Revenue Operations teams which includes more than 50 people. Adam has launched 3 new products into the market and grew organizations on the Gloo platform from 1,000 to 20,000+. 

He is also a Member at Revenue Collective.


Josh Braun

Speaker, Book Author and Renowned Expert on SDR Sales Teams

Since Josh’s childhood, he was passionate about teaching others. By the early 2000s, Josh Braun became a full-fledged salesperson working for a tech company. For a long time, he kept the two worlds of sales and teaching separate, thinking that they had nothing to do with each other. But the more he sold the more he realized that the worlds of teaching and selling aren’t that different. They both require to connect with audiences in compelling ways, to tell stories and most of all, to make other people happier. Josh found a way to bring these two worlds together in his books, courses and workshops. Now he is doing the thing he loves – teaching – while sharing the sales knowledge he has accumulated.

In this episode:

  • Learn about Josh Braun and how he went from an English teacher to a renown Sales Expert with a massive and active LinkedIn following all while being a Triathlon pro
  • The power of "heard and understood"
  • Why you shouldn't overcome an objection but align with it
  • How Josh implemented the FBI negotiating and communication techniques in sales
  • How to use mirroring, labeling and the accusation audit in sales prospecting just like Chris Voss
  • What is a late night DJ FM voice and why it matters for sales
  • Using "illuminating questions" vs leading questions and creating an information gap
  • What is Play #41 in the Bad-Ass Sales Guide
  • How to "detach from the outcome" to win in sales
  • What is a "commission breath" and how to rinse it out
  • Avoiding the "Yes Trap" and going with a No

Cory Bray

CEO, ClozeLoop & Best-Selling Author of 7 books

Cory Bray is the CEO of ClozeLoop, prominent sales thought leader and author of The Sales Enablement Playbook.

Before his career in ClozeLoop, Cory had previously built the sales onboarding program at another company, but he quickly learned there’s a huge difference between sales onboarding and actually closing deals.

Cory Bray is the Author of 6 books (and 4 more on the way). A major in Economics from Wharton who talks about scaling sales teams.

His books (all with 5 star reviews): 

  • The Sales Enablement Playbook
  • Sales Development: Cracking the Code of Outbound Sales
  • Triangle Selling: Sales Fundamentals to Fuel Growth
  • Sales Playbooks: The Builder's Toolkit
  • Hiring, Onboarding, & Ramping Salespeople: The T.E.A.M. Framework
  • The Five Secrets of a Sales C.O.A.C.H

In this episode:

  • How you go from Wharton to sales
  • Why Cory wrote a book about Financial Modeling for Sales
  • What exactly is Sales Coaching and why is it important
  • About Triangle Selling (and how it connects to Chicago Bulls)
  • and lots more!

Chris Cabrera

Founder & CEO at Xactly

In this discussion, hear from Chris Cabrera, Founder and CEO of Xactly as he talks about the ways to inspire and incentivize a sales team. Chris took Xactly public in a successful IPO and also took it private with Vista Equity, accomplishing something that makes him a unique CEO among the most successful CEOs in SaaS.

Chris Cabrera was recognized as a Top-50 SaaS CEO by The Software Report. Chris is an expert in Sales Performance Management and Sales Compensation. He is a seasoned executive with senior management experience who has led sales, operations, marketing, and business development. Also, Xactly won Best Place to Work 19 times under Chris Cabrera's leadership. Chris also shares how he got fired and how this experience led him to become a highly successful CEO.

Cory Bray is the Author of 6 books (and 4 more on the way). A major in Economics from Wharton who talks about scaling sales teams.

In this episode:

  • What is the "Rule of 10" (from the Vista Equity "playbook") and how to incentivize it
  • Incentivising your sales force for negotiating "5 year contracts where every year the $ACV increases"
  • Examples of sales data to make the CRO job’s 10x better
  • Leveraging insights from real compensation data & benchmarks
  • How many measures you should have on the comp plan
  • On comp plan insights that drive the best behavior and why SPIFFs are very effective
  • About the Corporate Culture for CEOs and Sales Culture for CROs
  • What is "C.A.R.E." and why it drives the culture
  • Advice for CROs who want to become CEOs (and why many CROs become successful CEOs)

Joe Caprio

EVP of Sales & Co-Founder,  Reprise

Joe Caprio is a cofounder at Reprise, a no-code platform for product demo creation, and recent VP of Sales at Chorus.ai. Joe also works in Parlor.io as a Strategic Advisor, so he is a real professional in getting practical advice about building, growing, and enabling sales teams to better connect with customers.

In this episode:

  • How Joe scaled Chorus.ai 100% - 200%+ per year to Series B round
  • Buyer vs. Seller conflict and friction and how to fix it
  • One big new trend in SaaS selling
  • On your AEs not demo'ing effectively
  • About 3 questions every new VP of Sales
  • How to be intentional in managing a sale cycle
  • What to do instead of asking Discovery questions
  • On what is the goal of a Demo

Frank Cespedes

MBA Class of 1973 Senior Lecturer of Business Administration at Harvard Business School

Frank Cespedes has run a business, served on boards for start-ups and corporations, and consulted to many companies around the world. He is the author of six books and many articles in Harvard Business Review, The Wall Street Journal, California Management Review, and other publications.


David Cichelli

Book Author, Leading Sales Compensation Expert, Advisor to multiple Billion-dollar companies

David Cichelli is with the Alexander Group, a revenue growth consulting firm. David helps companies achieve their sales objectives through a variety of solutions, including improved segmentation, channel design, sales ROI, sales metrics, quota allocation, selling models and sales compensation. David is widely recognized for his work in linking sales compensation to management's objectives, He is author of Compensating the Sales Force: A Practical Guide to Designing Winning Sales Reward Programs and The Sales Growth Imperative: How World Class Sales Organizations Successfully Manage the Four Stages of Growth. He is an instructor/author for WorldatWork’s classes on sales compensation. Mr. Cichelli holds an undergraduate degree from Pennsylvania State University and a graduate degree from Michigan State University.

In this episode:

  • Are variable incentives in the Sales Compensation even necessary if there are claims out there that sales people are driven by meaning and autonomy?
  • Discussion on how humans respond to a measurement system & alignment
  • Shouldn’t all salespeople have unlimited pay, like real estate agents?
  • Distinction between market makers ir income producers (100% variable & uncapped) & sales representatives
  • On the definition difference between a Commission (at risk) and a Bonus (add-on), and all other fun talk on things ranging from Target Incentives, to Quotas, to ICRs (Individual Commission Rates)
  • What is 3x Uncapped all about
  • Don’t pay programs reflect industry practices? One industry pays one way; another differently.
  • Discuss sales comp principles and how they apply uniformly; including globally.
  • How often should the pay plan be revised and why do companies change their sales compensation plans annually
  • Should a lot of pay be at risk-low base; high upside incentive? Concepts of pay mix and leverage-upside potential
  • Who should own the sales compensation plan? CRO/EVP of Sales? HR? Finance? Is it a program with a “shared responsibility” among various stakeholders.
  • What’s the purpose of quotas and how do they affect sales compensation. How quotas set expectations and equalize earnings for dissimilar size territories.
  • Who should be eligible for sales compensation - for instance, should Sales Engineers be eligible and who are the roles that truly persuade the customer to purchase.
  • How many "performance measures" should be in an incentive plan, including profit? Can you have more than 3? And what are the “output” measures that the seller can influence.
  • Should things like taking good notes in the CRM be one of the key measures in the incentive plan for reps.
  • How often should the incentive plan pay? Why it is tied to sales cycle, pay mix and cash flow considerations.
  • Is double crediting bad for two different sales reps in various situations? We discuss the implications of multiple sellers (aka persuaders). What factors should serve quota retirement/relief.
  • Should there be a clawback clause in Sales Comp Plans?
  • Why the revision to the sales compensation is a time to discuss objectives for the next year and is an excellent communication/leadership opportunity?

John Davagian

Senior sales and management leader

John is a dynamic senior sales and management leader with measurable business building success in the software industry. He grows revenue and profitability through attention to detail, efficient sales engagements, and streamlined processes leading to new customer acquisition, customer expansion, business development, and outstanding customer relationship/retention management. John developed and operationalized GTM strategies that yield significant growth (100-300%) year over year to achieve $100M annual run rates

In this episode:

  • How John went from being a Finance major into Sales (and why this helps him be one of the best CROs)
  • Why being very analytical & data-driven (as a Finance major) is crucial to be a successful Sales Leader today
  • How John grew sales from $1 Million to $65 Million at Salsify
  • Why confidence (and how to bounce back) is so critical in sales
  • On metrics like PPR, Productivity Yield, Pipeline Growth, Pipeline Aging
  • Esprit de corps on the sales floor, on making win and how that is so important
  • On building a Winning Sales Culture and how the concept of Winning changes
  • How productivity is affected as you get bigger
  • Why a Win Rate of 60% is a bad thing and why there is really no such thing as Win Rate of 30% or 50% or more
  • How "Closing the Aperture" on your market and prospects can help you grow faster
  • About driving your $ACV (is it messaging, product features, pricing, etc.)
  • Focusing on Expansion sales can yield exceptional growth beyond just New Logo Sales
  • What is an "Enterprise Sales" and on whether there can ever be a unified definition in SaaS

Mark Donnolo

Founder and Managing Partner of SalesGlobe & Book Author

Mark Donnolo is the author of many books and articles including:

  • The Sales Growth Imperative: How World Class Sales Organizations Successfully Manage the Four Stages of Growth
  • Quotas! Using Design Thinking to Solve Your Biggest Challenge
  • and other books for sales leadership

Mark Donnolo is also the founder and managing partner of SalesGlobe, a leading sales advisory firm focused on solving your biggest sales challenges. Areas of focus include sales strategy, customer segmentation, channel strategy, sales organization design and deployment, performance management, and incentive compensation. For over 25 years, Mark has worked with Global 1000 organizations on strategies to grow revenue.

In this episode:

  • How Sales Compensation is all about solving problems
  • Why Sales Compensation is "human" (and it's not just a formula)
  • What is a Revenue Roadmap and why it relates to Sales Compensation
  • Hear about how many measurements & accelerators you should have
  • How setting quota too high is a major problem in sales organizations (if not the #1 according to Mark)
  • How much should each measure represent in a sales comp formula
  • On average why only 42% of reps are benchmarked to be above quota
  • When setting Sales Comp strategy, how much % of your reps should actually hit their quota target
  • The 3 factors for setting correct quota - 1. Predictability, 2. Cost of Sales and 3. Motivation
  • What does "Winning Ugly" mean
  • How better "Challenge Questions" expand your thinking
  • The 3 linchpins of solving your quota - 1. People, 2. Marketing Opportunity, and 3. Sales Capacity
  • Best practices of measuring Sales Capacity: Sales Time Allocation, Level of Workload, and Quality of Talent (& using a Sales Time Optimization Tool)
  • On Performance Distribution and Over-Allocation ("padding") and uplift of the sum of AE goals when setting Quota for the team and the Board
  • Why and how CROs / EVPs of Sales need to educate PE and VC investors

Kevin Dorsey

VP of Sales,  PatientPop

Currently the VP of Inside Sales at PatientPop, Kevin has had an extensive sales career. He's been listed as an InsideSales Top 10 Sales Leader and Sales Development Exec of the Year, and his REVstar nomination called him "a true leader who can combine the vision it takes to plan ahead down to the day-to-day with the sales reps he's helping."

In this episode:

  • How do you use Analytics and tie it to humans (re data & Human element)?
  • How do you drive behavior change?
  • How KD scales sales faster - if the board asked to figure out a way to grow much faster in 2021, how he would approach it.
  • Thoughts on Behaviors vs Processes vs Skills vs Metrics
  • About managing Process vs developing People and skills
  • Leadership style of Demanding vs. Commanding
  • About "slowing down to speed up" and rebuilding and resetting to go faster
  • What are the biggest mistakes KD made in his career (one relating to how to communicate to the Board of Directors about "risks")- Board Talk - on the balance of Risks vs. Upside when communicating messages to the Board
  • What KD does when he is behind the goals in any Qtr (and the How vs. What vs. Why of either missing or hitting your numbers)
  • The key reason why, when the quota is missed, KD is still perfectly OK
  • And what is the reason that, when the team hits quota, KD is unhappy
  • About the concept of "Defend when Defendable"
  • What is "POE" and why it is the most important thing in sales
  • On Specialization vs. the prospecting AEs and the insight of AE1 vs AE2
  • Asking the question "Is it working?" first and foremost
  • About developing a training Bootcamp for new AEs promoted from SDRs
  • KD's insights on "earning promotion, not earning the role"

Armand Farrokh

Director of SDR + SMB @ Carta, Host of 30 Minutes to President’s Club, SDR Leader of the Year

Armand Farrokh is a Senior Manager of Sales Development at Carta that helps companies, investors, law firms, and employees manage equity.. He has a winning formula that is allowing him to crush quota repeatedly. Hitting 100% of quota is one thing but getting above 200% is a whole new ball game.

Armand leads a team of 30 SDRs and 3 Managers and he pays close attention to coaching his sales people make better cold calls.


Brent Gleeson

Founder & CEO at TakingPoint Leadership, Founder at Veteran Wellness, Navy SEAL, Keynote Speaker, Best Selling Author 

Brent Gleeson is a Navy SEAL combat veteran with multiple combat deployments to Iraq and Africa. Upon leaving SEAL Team 5, Brent turned his discipline and battlefield lessons to the world of business and has become an award-winning entrepreneur, bestselling author, and acclaimed speaker on topics ranging from resilience, mental toughness, leadership and building high-performance teams to culture, and organizational transformation. 

Brent is the Founder and CEO of TakingPoint Leadership, a progressive leadership and organizational development consulting firm with a focus on business transformation and building high-performance cultures. Brent was named a Top 10 CEO by Entrepreneur Magazine in 2013. 

Brent holds degrees in finance and economics from Southern Methodist University, certificates in English and History from Oxford University in England and a graduate business degree from the University of San Diego. He is the bestselling author of TakingPoint: A Navy SEAL’s 10 Fail-Safe Principles for Leading Through Change, which was a #1 New Release on Amazon in Organizational Change and Business Structural Adjustment. Brent latest book, Embrace the Suck: The Navy SEAL Way to an Extraordinary Life, publishes on December 22, 2020.


Richard Harris

CEO, Harris Consulting, Inventor of N.E.A.T. Selling, Speaker

Richard Harris has 20+ years of sales and SaaS experience. Richard has worked at or as an adviser or consultant with Visa, Google, Zoom, PagerDuty, Headspace, and Gainsight. He also hosts "The Surf & Sales" podcast with Scott Leese. 

Richard has been named a Top 25 Inside Sales Professional by the American Association of Inside Sales for the last four years and has been voted as a Top 10 Sales Development Leader by Inside Sales and Sales Hacker. He has also been published in Huffington Post, Inc, and most recently NBC News.

In this episode:

  • Richard's "best sales question ever"
  • The RESPECT Contract in sales
  • Trust / Circle of Trust
  • Earning "the right to ask"
  • Nuggets on sales questions to ask
  • Getting "Access to Authority" and Richard's key question to ask
  • The difference between Discovery & Qualification in sales
  • How PE and VC investors can better prospect to source deals
  • A tactical advice to improve your mental health in sales and reduce stress going into Q4
  • Wanting to talk to @Manny Medina, CEO of Outreach & @Henry Schuck, CEO of ZoomInfo

Jeff Hyman

CEO, Best-selling Author of "Recruit Sales Rockstars: The 10 Step Playbook to Find the Winners and Ignite Your Business", Professor at Northwestern University

Jeff is sure that 90% of the business problems are hiring problems in disguise. How would he know? Jeff is a four-time CEO, who recruited 3,000 professionals. And he simply refuses to let you hire a B-Player. Inc Magazine called him The Matchmaker because he has devoted his entire career to finding the best talent & teaching companies how to do the same. He built a remarkably simple, yet powerful, system for companies to scale past their competition with an unbeatable team of A-Players.

In this episode:

  • How to recruit A-Players for your Sales team
  • What is the ideal # of interviews
  • Secret of the Pros: what is the most "predictive" in interviewing and finding top performers
  • Surprising insight - why the interview itself is not predictive
  • Why to stop over-indexing on industry experience and why it does not matter much
  • How to hire (like Bill Belichick) - under-valued high-performance and high-achieving candidates that nobody hired yet who are the next Tom Brady, Julian Edelman and other top performers

Sam Jacobs

CEO, Best-selling Author of "Recruit Sales Rockstars: The 10 Step Playbook to Find the Winners and Ignite Your Business", Professor at Northwestern University

For the past 15 years, Sam has helped companies scale from just north of $0 in revenue to just shy of $300M. During that time, he’s developed deep operational expertise with particular emphasis on go-to-market strategy and execution mainly with SaaS and recurring revenue businesses. He’s been a commercial operator at GLG, Livestream/Vimeo, The Muse, and Behavox. 

Revenue Collective was created based both on Sam’s personal experience and the experiences of his friends, partners, and colleagues in the high growth community. 

He also hosts the Sales Hacker Podcast.


Jason Jordan

Founding partner of Vantage Point Performance

Jason Jordan is a founding partner of Vantage Point Performance, a global sales management training and development firm, and co-author of Cracking the Sales Management Code. Jason is a recognized thought leader in the domain of business-to-business sales and teaches sales and sales management at the University of Virginia’s Darden Graduate School of Business.

In this episode:

  • What Jason learned from research for "Cracking the Sales Management Code" and running companies between $20 Million in sales to $450 Million in sales
  • What makes a good sales team or Sales Leader
  • Why a sales team or Sales Leader that missed their team quota target is not necessarily a bad team
  • Inversely, why a Sales Leader or salesforce that hit their target is not necessarily good
  • It's not about metrics but about which behaviors and outcomes you want
  • Figuring out what drives Business Outcomes / Results
  • What is the difference between Data, Reports and Insights
  • Why having too many reports in your CRM is not what you want and what you should be looking for
  • On Leading Indicators vs. Lagging Indicators
  • Discussion on how you cannot manage Sales Outcomes / Results even thought that is what everyone always talks about at the Board of Directors meeting
  • Why the Board and PE / VC investors should spend more time with their portfolio CRO / VP of Sales
  • Why an Incentive Plan should be called a Reward Plan
  • What is sales team productivity (and efficiency vs effectiveness in sales)
  • How your Pipeline Mix analysis can help you avoid missing your number
  • What to do if you are behind your number and how to communicate to the CEO and to the Board and PE/VC investors if you are not going to attain the sales target any given quarter or year
  • On simplification of creating just 3-5 simple metrics for each separate role and why that's important

Scott Leese

CEO, Renowned Sales Expert, Founder of SurfAndSales.com Community

Scott Leese is one of the top startup sales leaders in the USA. Through domestic and international consulting as a strategic advisor; he has trained an army of salespeople and sales leaders thousands strong. Leese puts his nearly two decades of sales and leadership experience to use as the CEO/Founder of both Scott Leese Consulting, LLC and SurfandSales.com.

Scott is a 3-time winner of the Top 25 Inside Sales Professionals by the American Association of Inside Sales, and a highly sought-after consultant, advisor, leader, and sales trainer. While learning both the fundamentals, and higher strategy of sales, Scott Leese’s students come away motivated, and empowered. He has helped to create many successful organizations and has shaped thousands of individuals into highly sought after sales leaders.

In this episode:

  • Why Scott thinks any problems encountered in day to day sales are no biggie and how to learn from Scott's experience to look at life and sales differently
  • How Scott founded Thursday Night Sales which is the biggest such podcast and community in the sales world
  • How Scott created large presence and brand awareness
  • About how every professional wants to play on a Championship Team
  • Why messaging focus is so important
  • What are the biggest problems Scott sees in companies when he helps them grow
  • Why these are so important: getting your ICP right, building a great Sales Playbook and having a Sales Process
  • A big lesson of what most companies do not have enough of and where every company under-invests but really should not
  • What happens when you are 1 degree off course in sailing navigation and how that's relevant to leading sales teams
  • Where to find great sales talent - the one great place where you'll find it today

Chris Lytle

Book Author and Leading Expert on Sales Management

Chris Lytle has conducted more than 2200 seminars throughout the English-speaking world. A gifted speaker and teacher, Chris inspired and educated countless radio advertising sales professionals for 44 years. He is famous for providing “more usable information-per-minute” than anyone else in the business.

Chris is the author of the business bestsellers, The Accidental Salesperson: How to Take Control of Your Sales Career and Earn the Respect and Income You Deserve and The Accidental Sales Manager: How to Take Control and Lead Your Sales Team to Record Profits. His company, Instant Sales Training, continues to deliver his sales training in easily digestible knowledge bites. This automatic sales improvement process revolutionizes the way sales managers develop the people who develop their profits. Chris’ mission is making successful people and companies even more successful.

In this episode:

  • About the "Forgotten Rookie" & Sales Management Trap
  • Why there is so much risk when promoting an AE to a Sales Manager
  • How a new Sales Manager mitigates the "Unknown Unknowns" in the role
  • Why companies do sales training yet they don't do manager training
  • Where to focus as a priority - why a Sales Manager is more important as a driver of results than sales reps
  • Why companies promote their A-Players and top performers away from the role where they are highly successful into a role where they don't know anything about and don't always perform well as a manager
  • How and why sales are won in the Discovery phase
  • What makes someone a good sales rep & the value-add concept
  • What is a Sales Pipeline Angioplasty and how to purge out unlikely Opps
  • The difference between Prospects & Information Seekers and about engagement metrics and next steps in the sales process


Paul Melchiorre & Mark Petruzzi

Paul is an Operating Partner at Stripes, Co-author of "Selling the Cloud"

Paul is an Operating Partner at Stripes focusing on SaaS portfolio companies, specifically assessing and advising on go-to-market strategies. Currently, Mr. Melchiorre is an independent director at R3, an enterprise blockchain technology company, and was previously an independent director at Scout RFP, a sourcing and procurement software company that was acquired by Workday (NASDAQ: WDAY). He also sits on the board of nonprofit Spark.Org. Previously, Paul also served as Global Customer Officer and Chief Revenue Officer at Anaplan, a leading SaaS platform to facilitate financial planning and management, where he contributed to a successful IPO in 2018 and saw the company grow from $80 million to $300+ million in Annual Recurring Revenue and to over a $7 billion market cap.

Mark is a Co-author of "Selling the Cloud"; Vice President, Private Equity Go-To-Market and Corporate Partnerships at N3, part of Accenture.

Mark Petruzzi has worked in the enterprise software and cloud software ecosystem for 25 years. Today he is an industry leader with a distinct focus on channel and alliance program development and execution. 

Mark started his career at The MAC Group, a Harvard-based strategy consulting firm, and has held senior leadership positions at Deloitte, Oracle, Ultimate Software and HCL, driving exceptional growth and consistently delivering over-target revenue performance. 

In addition to his operating success, Mark is an author, speaker and an adjunct faculty educator at Duke CE, Trusted Advisor Associates and The R Group. He specializes in Cloud Software Sales, Trust-based selling and Cognitive and Behavioral-based Sales Team Development.

In this episode:

  • Insights from the new book "Selling the Cloud: A Playbook For Success In Cloud Software And Enterprise Sales"
  • How enterprise software selling has changed over time and the acceleration of those changes with the current environment around the work from home efforts
  • What is the future profile of the top enterprise sellers and how to identify them and compete for the scarce talent
  • How has the role of Customer Success evolved and where do you see its role in the future of the high growth SaaS companies

Justin Michael

Founder of the SalesBorgs

Justin Michael is the founder of the SalesBorgs, a new community for sales and revops. He is also Technologist & Consultant at Justin Michael Consulting. Over the last 20 years as a technologist and consultant, he has developed and refined the most advanced sales development techniques known to the world. These word-of-mouth only tactics, secretive until now, made Justin one of the most sought-after talents globally. Received a prestigious 10X Award by setting the industry record for 6 years of pipeline creation in 6 months.

He has cracked top of funnel sales development at over 100 startups and tech companies: Salesforce, ExactTarget, LinkedIn, and worked for Sean Parker. Mark Whalberg even hired him to train his team on LinkedIn strategy! Sellers trained on the COMBO PROSPECTING METHOD co-developed with Tony J. Hughes have produced over $100MM in qualified pipeline globally. As a certified Sales IQ Gold Partner, he has personally trained top sales reps worldwide enabling them to pull 7 figures.


JD Miller

Leading at the Intersection of Business, Technology and Humanity, Board Member, Conference Speaker, C-Level Executive

As a sales-oriented executive leader, JD Miller has a long track record of working with PE-backed or pre-IPO firms through their growth into very large public companies. His special skills and advisory experience includes leading sales transformations, building high-performing sales teams, and implementing quick growth/sales strategies with an eye towards operationalizing and formalizing approaches needed by large public companies.

 As a true "SMarketing" advocate, JD Miller also brings a lot of experience in bridging the gap between sales and marketing, with an emphasis on content-based marketing, social selling, account-based marketing, and web 2.0/social media strategy.


Mike Moorman

Managing Principal Sales Business Area and Practice Leader B2B Commercial Strategy & Transformation for ZS Associates

At more than 4,500 professionals, ZS is the largest consulting firm specializing in Sales and Marketing consulting, operations, technology and outsourcing. He is a leading expert in B2B sales strategy, sales force effectiveness and sales organization transformations.


Ernest Owusu

Sales Leader at 6Sense which is a SaaS company focused on ABM

Ernest Owusu is a Sales Leader at 6Sense which is a SaaS company focused on ABM. And he is a former NFL player turned Sales Leader who leads a 20+ person SDR team. This interview is about what Ernest learned in the NFL and what best insights he brings to leading his SDR / Sales Development teams which are focus on generating meetings focusing on accounts that lead to $100k+ deals.

In this episode:

  • How having stars doesn't guarantee winning and what you really need
  • How sales is easy compared to the cut-throat job of NFL - NFL players get fired for making 1 mistake or for being late to a meeting
  • His thoughts on why Latane Conant is the best CMO in SaaS
  • What is "Leadership" (beyond coaching) for you?
  • Using 3Cs to lead the team(Career, Culture, Compensation) vs. the 3Ds in the NFL
  • How to reinforce Culture via the "FAMILY" values (Fun, Accountability, Mindfulness, Integrity, Love, Yes)
  • Who was Ernest's favorite NFL coach and why (what made them a good coach)
  • What makes a good Team (good team building activities from NFL to Sales)
  • About effective recruiting and equipping yourself to spot intangibles (like Bill Belichick)
  • How Ernest coaches his team and what applies from NFL coaching to his Sales team coaching?
  • On ABM & Intent - how to use and fuel pipeline and sales growth

Chris Perry

President of Global Sales, Marketing and Client Solutions at Broadridge Financial Solutions

Chris Perry has 25+ years of senior sales, marketing and business leadership experience in financial information and technology companies. Whether leading a global team of 3500 to deliver sales, service and $7 billion in revenue or developing a modern strategy for delivering risk management solutions or building a start up business to explosive growth - Chris is a tech-savvy leader, with an inspiring presence, and a doer who is accustomed to leading client-facing activities to success.


Kyle Porter

CEO at SalesLoft

Kyle Porter is the founder and CEO of SalesLoft, the provider of the #1 sales engagement platform. SalesLoft helps more than 2,000 companies provide better selling experiences to their customers and was named the 7th Fastest-Growing Technology Company in North America by Deloitte. Recognized as the #1 best place to work in Atlanta for the second year in a row, SalesLoft has more than 400 employees in its offices in Atlanta, San Francisco, New York, London, and Guadalajara, Mexico. Kyle is a fervent champion of organizational health and is focused on creating an environment where people can learn more, do more and become more.


Jamal Reimer

Top 1% at Oracle, Leading Expert on Mega-Enterprise Sales (closed multiple $50M+ deal sizes)

Jamal Reimer is a Top 1% seller at Oracle. He is a "Mega-size Enterprise Sales" expert who has worked at Oracle and has sold exceptionally large enterprise deals, having closed nearly $200,000,000 in sales himself. He has also closed several deals that were $50 Million in size each and carried annual $30 Million+ quotas. He is a renown expert in very large size Enterprise Sales. He now coaches individuals and teams on how to find and close megadeals.

In this episode:

  • Difference between Enterprise Sales & Mid-Market Sales
  • Mapping out the buyer's Organization
  • Using data in pricing negotiations on Enterprise Deals
  • Establishing & defending pricing
  • Delivering "the Story of Value"
  • The "Investment Portfolio" enterprise sales method
  • How to build a "Relationship" in the Enterprise Sales motion
  • What to do when you miss your annual quota
  • Why Jamal wants to meet Thomas Kurian of Google Cloud

Keegan Riley

Chief Revenue Officer at Sysdig

Keegan Riley is a proven leader of field sales and he is a high-growth technology expert. 

“I worked with Keegan at Nimble Storage and I saw him succeed time and time again. One of his greatest strengths is selling a platform he believes in, capitalizing on both established and emerging markets, and scaling a channel”, - said Suresh Vasudevan, CEO, Sysdig.

Riley rose through the ranks at Nimble Storage, which IPOed at $1 billion. He has been credited with making massive contributions to their growth. Prior to joining Nimble Storage, Riley held sales leadership positions in global and enterprise accounts at HP within the Storage Division, sales roles at Dell EMC, and various technical and sales roles in entrepreneurial firms in other industries.


Paul Roetzer

Founder & CEO | Marketing AI Institute & PR 20/20

Founder and CEO of PR 20/20 and Marketing Artificial Intelligence Institute; author of The Marketing Performance Blueprint (Wiley, 2014) and The Marketing Agency Blueprint (Wiley, 2012); and creator of the Marketing Artificial Intelligence Conference (MAICON) and the AI Academy for Marketers.

As a speaker, Roetzer is focused on making artificial intelligence approachable and actionable, and helping change agents drive transformation through marketing talent, technology and strategy. A graduate of Ohio University’s E.W. Scripps School of Journalism, Roetzer has consulted for hundreds of organizations, from startups to Fortune 500 companies.


Richard Sgro

General Manager at Modern Sales

Richard calls himself a force multiplier. He is passionate about efficiently scaling revenue and business operational capacity in high growth organizations. His teams are in the business of being better prepared, more impressive, and more effective than the competitors. That’s why Richard is a successful General Manager at Modern Sales.


Fred Shilmover

CEO and Founder of InsightSquared

Fred Shilmover helped grow the revenue intelligence company from a single spreadsheet prototype into one of Boston’s premier software companies. Fred began his career in IT consulting. He joined Bessemer Venture Partners to run IT operations and later transitioned onto their investment team. During his time as a summer associate on the corporate development team at Salesforce.com, the idea of helping businesses make better decisions was born.

Fred is a board member of TUGG (tugg.org), an organization that brings together the Boston tech community to raise money and put philanthropic support behind Boston’s best new nonprofits. He has (slowly) run the Boston Marathon three times to raise raising money for TUGG supported nonprofits Fred graduated from Tufts University and Harvard Business School.


Jen Spencer

Vice President, Sales and Marketing at SmartBug Media, Speaker, Sales Mentor

Jen Spencer is the Vice President of Sales and Marketing for SmartBug Media, an Intelligent Inbound® marketing agency of experts in digital strategy, revenue operations, public relations, content marketing, and marketing automation. She's also a founding coach at SDR Nation and a past board member of the Phoenix chapter of Girls in Tech. Jen subscribes to the notion that “we’re all in this together,” and great communication leads to great partnership. She loves animals, technology, the arts, and really good Scotch.


Paul Szemerenyi

Vice President of Global Sales at Bizzabo

Paul is a Senior Executive with a demonstrated ability to build and manage high performing global sales teams. Over the last 20 years, he has proven experience at a variety of software companies. He initially started as a 1st Line Manager at larger organizations such as Veritas and Quantum, before pivoting into the world of Start-ups, where he knew he could make a difference. He has held numerous 2nd and 3rd line executive roles at hyper growth companies, such as Braze, AppSense and Bizzabo. At every one of these roles, he implements clear sales methodology and playbooks, that drive predictable and consistent results.


Stephen Thomas

Sales Leader, Business Builder, Board Member

A proven executive that delivers strong results while making a broad impact on the company and a personal impact on the team. Stephen Thomas is a collaborative and action-based leader that is focused on attracting and developing the team, engaging that team on the right strategy, ensuring execution of the plan, and decision making that accelerates the organization. He is influential at all levels due to his knowledge, communication style, and passion for the business.


Sangram Vajre

2x Author, Co-founder at Terminus, Host of the top 50 business podcast #FlipMyFunnel

Sangram Vajre has quickly built a reputation as one of the leading minds in B2B marketing. Before co-founding Terminus, a SaaS platform for account-based marketing, Sangram led the marketing team at Salesforce Pardot. He has spoken on the topic of marketing technology around the world and is the mastermind behind #FlipMyFunnel.

Sangram wrote two successful books on account-based marketing published: Account-Based Marketing For Dummies and ABM Is B2B.: Why B2B Marketing and Sales Is Broken and How to Fix It.


Kyle Vamvouris

CEO of Vouris, Best Selling Author

Kyle builds and scales world-class inside sales teams. He started his career as an SDR for a large tech company and was an account executive until he finally decided to take the plunge and write a book, Cold to Committed. It was well received and made it on the Amazon bestseller list in the categories Sales and Selling and Telemarketing.

Kyle has experience in training and mentoring all types of sales reps. He has scaled multiple inside sales teams and has led a front line team responsible for hockey stick growth leading to a successful series B funding round. He has deep knowledge of sales processes, sales tools, and management. Kyle is passionate about motivating individuals/groups as well as tailoring constructive feedback and training. 


Mike Volpe

CEO at Lola.com

Mike is the CEO at Lola.com, Spend Management & Travel Management Software

Previously, he has joined HubSpot as the fifth employee and as CMO helped the company grow from about a dozen beta customers to over 15,000 customers, 1,000 employees, $150m in revenue, and an IPO leading to a $1.7B market cap. He has also made more than 25 angel investments with 4 exits so far (HubSpot, Locately, GroSocial, ThriveHive).

Mike serves as an advisor to a number of companies and is on the board of directors of Repsly, a mobile CRM company and was on the board of Attend until they were acquired by Event Farm. He has worked in marketing at a number of different startups in Boston and San Francisco and loves talking about marketing and growth with other marketers and entrepreneurs.


Jeffrey Winters

President at Sapper Consulting

Jeff Winters is founder and CEO of Sapper Consulting, which replaces cold calling for its clients

Jeff and his team at Sapper Consulting take a human approach in this ever-increasing age of robots, AI automation and mass email campaigns. Great business opportunities start with the people who drive them. And with personal unique messages to each prospect, they leverage powerful emotional connections and inspire prospects to contact you...and not your competitor.

In this episode:

  • How Jeff wrote unique and funny emails that got him meeting with Morgan Stanley which caused him to leave his job and start a company that is now in the Inc 500 for 3 years in a row
  • How Jeff got to 800+ customers as a professional service organization in less than 8 years
  • What it means to create an environment where the deal can be easily closed and all the friction points you must remove ASAP
  • About a "1 page Contract" and what to tell your lawyers if they cannot do it
  • About creating a "low barrier to entry" to your Demo, Trial and to buying
  • On insight from Brian Halligan, CEO of Hubspot who said "Sell the way your customers want to buy"
  • On "Frictionless-ness as the key to a great sales process"
  • How to get sales meetings using the 5 key steps (i.e. ICP, TAM/Billable Market, who is the Decision Maker, define the prospecting strategy based on TAM, and chunk the tiers into Tiers 1/2/3)
  • Strategies and tactics to chunk and segment for macro, micro, and nano tiered accounts
  • How do you define the difference between Marketing vs. Sales “lead generation”?
  • What it means to creHow Marketing is "Long Tail Strategic" and Sales Development is "Short-Tail Tactical"ate an environment where the deal can be easily closed and all the friction points you must remove ASAP
  • The very incorrect definition of "Outbound vs Inbound" when it comes to your SaaS SDR prospecting teams & why you must stop conflating it with Attribution or Sales Compensation
  • Real benchmarks from the front lines on B2B SDR metrics - Cold Outbound Conversions and the Average Number of "Sales Meetings" Scheduled in SaaS by Outbound SDRs
  • How to use Mailchimp's data/stats to help yourself approximate and plan out your SDR meeting production bia real /pure Cold Outbound Emails
  • On MCR - Meeting Conversion Rate - and how it's so important
  • Top Secrets to successful SaaS prospecting including Accurate Contact Lists, Perfect Copy, Perfect Tactics, and Multi-Channel approach
  • What is Jeff's definition of “sales engagement” and thoughts on the future of sales engagement
  • Why SaaS is a philosophy and not just a model