On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Kyle Racki, noted author and CEO of Halifax’s Proposify.
In addition to leading Proposify’s growing team through fundraising rounds, the ups and downs of startup life, and a company-wide evolution to sell bigger deals, Kyle is a trained designer, former agency head, and noted author.
Throughout the pod, Collin and Kyle discuss Proposify’s move up market from servicing just small businesses to selling enterprise deals. Highlights include: Proposify...before moving up market (4:37), where did Proposify start price-wise to go up market? (7:49), Proposify’s initial sales team (11:29), the big changes (17:41), key realizations (24:24), re-training sales (33:24), the changes to customer success (40:38), and Proposify’s wins and mistakes (44:14).
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Nick Rathjen, Vice President of Account Development at Samsara.
Nick is a veteran sales professional – through and through. He has led sales teams at some of the biggest organizations in the world (Oracle) and fast-growing companies like Samsara.
Throughout the pod, Collin and Nick talk about hiring reps, maintaining cultures, and the importance of mentors. Highlights include: how to hire 200 reps in a year (17:50), establishing weekly goals for the company's different offices (21:24), team composition (28:35), Samsara’s onboarding (32:51), Post onboarding structure (39:57), Samsara’s sales playbook (52:46), the importance of Mentors (1:05:25), and proud moments (1:13:21)
Show Notes: Nick’s onboarding workbook
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Meganne Brezina, Senior Manager of Sales Enablement at Emarsys.
With a wealth of experience at some of tech’s largest companies, Meganne is a veteran sales enablement manager...and expert sales kickoff planner.
Throughout the pod, Collin and Meganne discuss how to plan an exciting, educational and, let’s face it, fun sales kickoff event.
Highlights include: why do a sales kickoff? (5:12), how big does your company have to be to host a sales kickoff? (7:12), who gets invited? (10:18), what aspects do you absolutely need to nail at these events? (11:39), how to avoid making it a “drinking event” (18:42), designing an agenda (21:56), impact (25:10), keeping focus throughout the year after your event (27:46), the sales lightning round (33:47), and cold call Collin (37:50).
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Laurabeth Harvey, Senior Vice President of Sales, Success, Support at Intercom.
Laurabeth has held nearly every leadership position there is to have in sales: manager, director, VP, SVP...Laurabeth has seen a thing or two. And she’s on the show to discuss her journey, and impart some wisdom she’s learned along the way.
Throughout the pod, Collin and Laurabeth discuss how to stand out as an early frontline sales manager, and how to make the jump to more senior (and strategic) leadership positions. Highlights include: Laurabeth’s sales journey (36:13), how to stand out and get tapped for the big jobs (39:55), the importance of prioritization (42:00), getting the right people on the bus (55:27), improve the organization (1:00:13), making the right decisions...quickly (1:05:47), and decision making frameworks (1:14:15).
Links from the podcast
LB’s LinkedIn - https://www.linkedin.com/in/laharvey/
DACI Framework - https://www.atlassian.com/team-playbook/plays/daci
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes troy Conquer, Chief Revenue Officer at fast growing revenue operations consultancy Go Nimbly.
Troy has a somewhat different background from the dyed-in-the-wool sales professionals we typically have on the show. Trained as an engineer, Troy has extensive experience as a consultant and a developer, before taking on the task of leading sales at Go Nimbly.
Throughout the pod, Collin and Troy discuss the fluid, and tricky, art of selling services. Highlights include: honing in when you sell services (18:54), crafting bespoke plans and roadmaps (22:05), the evolution of Go Nimbly’s sales process (27:17), the Go Nimbly discovery call (49:44), sharing the right amount of detail (54:11), submitting proposals (1:07:29), the sales lightning round (1:12:18), and cold call Collin (1:16:31).
Discover one new episode every week!
At Predictable Revenue, we live and breathe outbound sales. We’ve found that too often, outbound sales initiatives are driven by instincts and gut feeling. We decided to use the scientific method to test the latest trends in outbound sales. We’ve run over 50 outbound experiments, and plan to continue running 10 to 20 experiments a month. We’ll be sharing the results of our experiments and the conclusions through our Outbound Labs video series. Throughout the series, we’ll highlight what’s working and what isn’t in Outbound Sales, keep you up-to-date on the latest trends and help you increase your sales.
We just wrapped with Robbie Allen, Founder at Buena Vista Ventures. You might also recognize him from his time at MixMax, Flexport, or that time he helped hire 250 sales reps at Zenefits. We dug deep into scaling sales teams and discussed the three stages that every startup sales team goes through: Product Market Fit (finding a mismatch), Repeatability and Scale (how to run a play repeatedly and see consistent results); and Hypergrowth (where you have a full playbook).We also talked about what sales ops, enablement, recruitment & hiring look like in each stage, and what are some of the biggest missteps you can make.Some of the highlights include:
Defining the 3 stages and what needs to be done differently in each one.
The goals behind each stage.
How to get ready for the next stage.
Learning to be a strong sales ops leader
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Kaitlyn Buckheit, Sales Development Manager at Lever.
Kaitlyn is a veteran startup sales leader and compassionate manager working to empower her teams to not only crush their numbers, but cultivate a mindset that will empower them in all areas of their life.
Throughout the pod, Collin and Kaitlyn do deep dive on creating and living that positive mindset. This is powerful stuff. Highlights include: defining and hiring for Mindset (4:17), Lever’s hiring process (21:40), “Aha” moments (31:55), coaching reps for mindset (44:52), living those new beliefs (1:00:47), sales lightning round (1:10:00), and cold call Collin (1:14:39’).
Interview question you can use to discover a candidates mindset: Tell me about a time the odds were stacked against you?
Tell me about one of your failures?
Tell me about the last time you went through a significant change in your current organization?
Explore further with follow up questions: Walk me through that.
Who helped with that?
Where did you come to that idea?
How did you feel about that?
How they talk about the process, and how they talk about the challenge will be a significant indication of if this person has the right mindset.
Links mentioned in the podcast:
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes David Dulany, Founder and CEO of outbound sales consultancy Tenbound.
If you look up “salesperson” in the dictionary, there may as well be a picture of David. He’s led sales development teams of all sizes, created prospecting teams from scratch, and hosts a terrific (and aptly-titled) Sales Development Podcast.
Throughout the pod, Collin and David discuss how to empower your SDR team to nail your event outreach. Highlights include: why host / attend events? (21:08), getting the most out of your events (35:11), the role of AEs in events (46:04), the role of managers in events (58:02), why should people come to The Sales Development Conference? (103:58).
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Andrew Oddo, Director of Growth at Bowery Capital.
Andrew is a veteran sales professional who turned VC. He’d helped countless growing companies build their outbound sales machine, as well as crushed a quota or two in his time.
Throughout the pod, Collin and Andrew do deep dive into early-stage sales planning. If you’re a budding company looking to solidify your sales process and grow your team – this pod is a must-listen.
Highlights include: Andrew’s sales journey (7:44), the benefits of a documented sales playbook (11:50), the pieces of the playbook (19:07), the ICP and buyer persona (22:30), channels and messaging (32:44), arming your team (47:12), maintaining quarterly playbook reviews (59:31), sales lightning round (1:03:44), cold call Collin (1:10:03).
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Sarah Harbison Tosh, Senior Director Market Development at marketing platform Sigstr.
Sarah is a veteran sales leader – she’s grown and managed teams at startups, fast-growing mid-market companies, and international tech unicorns.
Throughout the pod, Collin and Sarah discuss the growing trend and power of mixing brand marketing with outbound sales development.
Highlights include: why brand is getting involved with outbound (4:39), striking the right balance between creativity and numbers (6:13), using creativity, personalization, and scale to stand out (9:33), staying on brand while giving SDRs freedom to be creative (16:23), teaching authenticity (43:50), the power of events (46:39), G2 Crowd reviews (58:40), sales lightning round (101:14), and cold call Collin (1:04:17).
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Jeff White, Founder and Principal of Kula Partners.
Jeff is a veteran entrepreneur, marketer, and content creator – most notably known for creating the popular Kula Ring Podcast.
Throughout the pod, Collin and Jeff discuss how to leverage content to drive prospecting and, of course, pipeline. Highlights include: Jeff’s content philosophy (3:56), the power of podcasting (9:43), Kula’s post-podcast outreach (16:20), Kula’s suite of content (24:12), the executive roundtable (39:02), the sales lightning round (47:46), and cold call Collin (56:03).
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Lauren Bailey, founder of sales training and leadership consultancies Factor 8 and #GirlsClub
Lauren is a renowned sales trainer and entrepreneur: before founding her own companies and working as a freelance training consultant, she led global sales teams and training divisions at international software goliaths like SAP.
Throughout the pod, Collin and Lauren talk about a critical, yet often neglected, element of sales: cultivating confidence in reps.
Highlights include: how Lauren defines confidence (14:32), confidence killers (19:26), building confidence (24:30), the role of personality in confidence (41:15), how frontline managers can inspire confidence (47:46), the sales lightning round (56:12), and cold call Collin (1:00:50)
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Steven Broudy, Vice President and Head of Sales at San Francisco-based customer to customer community management platform Bevy.
From Army ranger sniper to SDR to renowned sales leader at some of the Bay Area’s most well-known companies, Steven has had one interesting journey into sales.
Throughout the pod, Collin and Steven take a look at the next skills, trends, and tactics that will define the next decade of sales. Highlights include: Steven’s sales journey (12:29), the evolving B2B sales cycle (22:28), meeting buyers where they are (30:53), and empowering salespeople in an environment of eroding trust (50:02).
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Kelly Del Curto, Director of Small Business and Corporate Sales at lever.
From starting as a quota-carrying rep, to running multiple sales teams, to hiring for a rapidly growing sales org – Kelly’s done it all during her tenure at Lever.
Throughout the pod, Collin and kelly do a deep dive on a critical yet underserved aspect of sales (and team building as a whole): effective goal setting.
Highlights include: Why investing in long term coaching is the right move (1:51), team goal setting (5:06), individual goal setting (27:38), strengths and saboteurs (39:19), putting it all into action (52:05), sales lightning round (1:02:55), and cold call Collin (1:05:43)
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Justin Clifford, Director of Sales at Lessonly.
Justin, by his own admission, grew up in sales: before leading the team at Lessonly, Justin held both leadership and quota-carrying roles in a host of different industries.
Throughout their discussion, Collin and Justin tackle a philosophical, nuanced, and undeniably important aspect of sales: inspiring your team to be themselves and excel at their jobs. They also talk about some inspiring reads, including the 15 Commitments of Conscious Leadership by Jim Dethmer, Diana Chapman, and Kaley Klemp. Check it out, if you haven’t already.
Highlights include: unlocking growth in your reps (22:16), Justin’s approach to leadership (27:04), the importance of being vulnerable (30:20), the autonomy to get your teeth kicked in (41:58), value-adding moments (57:20), how Justin does his forecast reviews (1:09:07), the sales lightning round (1:18:31), and cold call Collin (1:24:59).
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Nicolas Marchais, Head of Sales at Spendesk.
Since he joined the company when it was just a two-person startup, to leading an international sales team, Nicolas has seen at all at rapidly-growing spend management platform Spendesk.
Throughout the pod, Collin and Nicolas take a trip down memory lane and recount the mistakes and lessons learned from Spendesk’s rapid growth. Highlights include: Nicolas’ history at Spendesk (5:50), Spendesk’s rapidly-growing sales steam (10:28), mistakes made along the way (21:32), the importance of finding the right people (42:16), sales lightning round (58:23), and cold call Collin (1:01:18).
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Alexandra Adamson, Executive Director of sales advocacy organization Women in Sales.
From her time at renowned recruiting firm Betts Recruiting, to her tenure as Director of Talent at Bowery Capital, to her current role helping lead Women in Sales – Alexandra has been supporting sales professionals and sales teams for years.
Throughout the pod, Collin and Alexandra discuss how to find support (and give support!) in your sales career. Highlights include: Alexandra’s journey (14:36), Women in Sales (23:40), the subtle art of job descriptions (31:33), taking ownership of your career (33:07), finding a mentor (37:12), sales lightning round (49:14), and Cold call Collin (53:14).
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Dan Martell, renowned coach to SaaS founders.
In addition to his international coaching business, Dan is also a veteran entrepreneur (3 exits) and noted angel investor. Suffice it to say, Dan has closed a deal or two in his time.
Throughout the pod, Collin and Dan take a tour of all things sales, content...and philosophy. For example, Dan and Collin chat about consistency theory, the rule of three, and peak end bias. Oh, and they also analyze two of Dan’s foundational sales frameworks: his five key sales principles, and the rocket demo.
Highlights include: what is a demo, really? (15:02), Dan’s key sales principles (17:54), the Rocket Demo (38:25), Dan’s discovery calls (56:16), the sales lightning round (1:07:05), and cold call Collin (1:12:29).
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Jeremy Ellens, founder of fast-growing lead generation company LeadQuizzes.
Jeremy is a entrepreneur, turned sales leader, turned podcast host. When he’s not leading LeadQuizzes’ team (a role he’s navigating rather successfully), he’s talking with other sales leaders about how their secrets on the Journey to 7 Figures Podcast.
Throughout the pod, Collin and Jeremy talk about what every entrepreneur, sales leader, and quota-carrying rep is chasing: scalable revenue growth. Highlights include: taking LeadQuizzes to market (8:41), the importance of case studies (11:40), designing crafty lead generation tactics (13:29), learning cold outreach (16:58), perfecting the pitch (26:52), expecting objections (32:34), uncovering unique channels (38:36), and cold call Collin (54:00).
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Travis Henry, Director of Inside Sales Operations at renowned Bay Area sales consultancy SalesSource.
A respected sales operations specialist, Travis honed his skills global technology companies and has consulted for startups large and small. If you’re looking to grow your sales team – look no further, Travis is your man.
Throughout the pod, Collin and Travis do a deep dive – a very deep dive – on how to juggle sales automation and the ever-critical human element needed in prospecting. Highlights include: what’s bugging Travis? (2:30), remembering sales fundamentals (6:00), identifying gaps...and thinking outside the box (10:32), designing unique, human cadences (23:50), teaching reps to personalize emails (37:29), data infrastructure and your SDR team (58:11), sales tactics lightning round (1:06:56), and cold call Collin (1:08:39).
On this edition of the Predictable Revenue Podcast, co-host Collin Stewart welcomes Nishank Khanna, Co-Founder and CEO of Demand Roll, a full service marketing agency.
After starting six startups – two of which that were acquired – Nishank is a seasoned entrepreneur and marketer.
Throughout the pod, Collin and Nishank discuss an always fascinating problem: how to harmoniously integrate outbound sales and marketing. Highlights include: Nishank’s background...and how he got into a bit of outbound on the side (10:22), different ways sales and marketing teams can work together (12:58), producing content that converts (15:46), bottom of funnel vs. top of funnel leads (22:22), getting people to respond to emails (25:49), ad spending (43:51), and cold call Collin (1:00:11).
To celebrate the 100th edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes a familiar face back to the pod, co-host and co-CEO of Predictable Revenue Aaron Ross.
Who better to reflect on this awesome milestone with?
Throughout the pod, Collin and Aaron take a trip down memory lane and chat about the most valuable lessons and nuggets of wisdom shared on the podcast thus far. With the impressive roster of guests the show has had, boiling the down the best tips and tricks into one episode was no easy task.
Highlights include: Jeff Davis’ thoughts on organizational alignment and the importance of a revenue team (1:27), Jamie Buss’ mind-blowing forecasting process (12:42), the always important task of nailing a niche (26:00), Bill Binch’s consistent hiring process (38:28), Mark Kosoglow’s revolutionary discovery method (44:00), and Aaron’s thoughts on how to prioritize a never-ending list of tasks (49:55).
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Keith Cordeiro, Account Executive at Crosstex International and Host of the Philosophy Of Sales podcast.
On this episode, Keith shares the impact that meditation and mindfulness has had on his sales career. Keith detailed 3 different meditation styles any salesperson can use to cultivate a positive attitude:
Highlights include: finding meditation (7:33), the impact meditation has had on Keith’s career (10:14), cultivating a more present mind (16:37), getting started with meditation (25:53), sales tactics lightning round (48:13), and cold call Collin (56:08).
On this edition of The Predictable Revenue Podcast, co-host Collin Stewart welcomes Kyle Roach, Sales Development Manager at Lessonly.
After a career teaching high school Spanish and coaching competitive soccer, Kyle fell in love With Lessonly in 2016 and joined the sales development ranks immediately. He’s been there ever since.
Throughout the pod, Collin and Kyle talk about testing the pillars of sales development outreach, and why selling the dream is more important than selling software. Highlights include: Kyle’s journey (10:51), changing Lessonly’s sales org structure (12:23), establishing Lessonly’s “sell the dream” process (22:08), executing “selling the dream” (27:34), overhauling the Lessonly cadence (38:09), Lessonly’s cold call script (51:42),measuring the impact on Lessonly’s business (1:06:21), and cold call Collin (1:14:02).
Links we mention in the show: