MySalesDay

Jeff Zito: 30-60-90 Plans and Account Planning for B2B Sellers

Sun, 22 Feb 2026 20:18:26 +0000

Jeff Zito just accepted a new role as Regional Vice President at Cadent and he joins Michael Hess on the MySalesDay Podcast to break down the exact frameworks that help B2B sellers ramp faster and sell more strategically.

This episode tackles two topics that can change your year: building a practical 30 60 90 plan when you start a new role and running a simple account planning process that keeps you proactive instead of stuck “selling out of your inbox.” Jeff shares how he approached his own 30 60 90 request, why early credibility matters, and how to set realistic expectations around activity, meetings, and momentum. Then the conversation shifts into account planning, including account segmentation, retention risk, and relationship mapping so one contact is not a single point of failure.

If you are a B2B sales professional or sales manager, this is a playbook episode on speed to market, building pipeline early, and creating repeatable habits that compound over time.

Time stamps
00:26 Jeff Zito announces his new role as Regional Vice President at Cadent
01:39 Why 30 60 90 plans matter and how they connect to account planning
03:54 Jeff’s reaction to being asked for a 30 60 90 and how he built it
06:00 The foundations of a strong 30 60 90 plan: learn, diagnose, execute
08:44 What “closing” really means in the first 90 days and the value of mini wins
10:49 Setting expectations with your manager and how to sniff out unrealistic plans
11:58 First 30 days priorities: master territory, audit pipeline, prospect immediately
13:27 How to coach hesitant sellers and create early “layups” for confidence
15:17 What must happen in your first 90 days to set up a strong year
17:25 Prep work and organization as the hidden advantage in ramping fast
20:41 When new hires should be tested on objections, competitors, and messaging
22:01 The effort standard in modern sales and why the first week matters
27:01 Shadowing, role playing, and peer learning to accelerate readiness
30:15 Holding activity levels accountable and leading by example as a manager
35:39 Account planning as the shift from reactive to strategic selling
37:26 Segmenting accounts and focusing time where revenue is most likely
38:45 Protect, retain, grow: managing risk and finding white space
45:05 Relationship mapping to reduce risk and build multiple champions
47:52 The best plans are owned by the rep and built with follow through

Watch the full interview on the MySalesDay YouTube channel
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#MySalesDay #B2BSales #SalesPodcast #SalesMotivation

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Objection Handling That Wins Trust with Doug Weaver and Michael Hess

Mon, 16 Feb 2026 11:00:00 +0000

In this episode of the My Sales Day podcast, Michael Hess sits down with Doug Weaver to explore what happens when a long, successful chapter ends—and what the next one requires of modern sales leaders.

Doug reflects on the emotional reality of moving on from Upstream Group after a multi-decade run, why creating a “proper ending” mattered, and what it feels like to step into a new venture as a solo act. From there, the conversation shifts into a lesson Doug learned early in his career that reshaped everything: stop focusing on your own performance and start focusing on what’s in it for them. In workshops, in sales calls, and in leadership—Doug argues the role is to be the host, not the entertainment.

You’ll also hear a powerful anecdote about a salesperson asking for “a strategy to make customers feel like I care,” and Doug’s blunt, human response: care. Not as a tactic—but as a choice that changes outcomes.

The second half opens a deep dive into objection handling—not as combat, but as service. Doug challenges the “comeback” mentality and offers a more effective objective: shorten the timeline to truth and expand the available information. The result is a practical, repeatable approach for sellers and sales managers who want more clarity, fewer stalled deals, and stronger buyer trust.

Featuring: Doug Weaver
Host: Michael Hess, My Sales Day

Timestamps

00:12 Leaving success behind: how emotional was it to move on?
00:59 Why the timing felt right and why Upstream Group was never “just Doug”
02:44 The most important lesson from 28 years helping sellers and managers
03:16 The turning point: performance vs. service—“be the host, not the entertainment”
04:40 Creating participation: drawing out the quiet voices in the room
05:16 Sustainability: why listening beats performing (two ears, one mouth)
06:21 The “strategy to make customers feel like I care” story—and the humanity lesson
08:02 The Weaver Collective: semi-retirement, coaching, and building the next generation
09:56 Why frontline sales managers are under-supported (and why this matters now)
10:43 Objection handling as the “whopper” skill—and why it’s never a one-and-done
12:06 You don’t need perfection: the goal is to shrink objections, not eliminate them
13:27 “We train humanity out of salespeople”—why objection handling isn’t conquest
15:17 Doug’s framework: ask meaningful questions before offering answers
16:07 The real objectives: shorten time-to-truth and expand available information
18:05 Slow down on the off-ramp: understand why they’re saying it
20:32 Anticipating objections before the call: role play, prep, and patterns
24:13 Why sellers struggle: weak questions, lack of structure, and rushing to “answer”
27:23 Objection resolution as service, not combat—and why practice builds confidence
34:09 Moving objections upstream: don’t wait until “late stage” to surface resistance

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Ryan Picchini on Self Appraisal: Build Better Habits and Close More B2B Deals

Tue, 03 Feb 2026 05:15:00 +0000

What separates good sellers from great ones usually isn’t hustle—it’s self-awareness.

In this episode of the My Sales Day podcast, host Michael Hess sits down with Ryan Picchini (CRO at dotCMS) to unpack a skill most sellers avoid: analyzing your own selling behaviors. Ryan explains why self-evaluation is the lever that improves win rates, strengthens relationships, and helps sellers build a repeatable path to performance—not just a lucky quarter.

You’ll hear practical ways to do self-appraisal even if your manager doesn’t coach, how to extract patterns from your calls and journals, and why top performers don’t stop “selling” when the deal enters late stage. Ryan also shares how leaders can coach tenured reps who think they’re “good enough,” and how a personal manifesto can drive the daily actions that produce long-term results.

If you want to sell with more intention—and improve outcomes without burning yourself out—this conversation gives you frameworks you can use immediately.

Featuring: Ryan Picchini, CRO at dotCMS
Host: Michael Hess, My Sales Day

Timestamps

00:17 Welcome back + why sellers avoid looking in the mirror
01:20 “If you don’t know yourself, it’s hard to know your customer”
02:01 Ryan’s new role as CRO at dotCMS and what changed
03:02 Skill gaps leaders must face: demand gen, partnerships, rev ops, deal cycles
04:10 Leadership as the multiplier: empowering the team vs doing it yourself
05:45 The core idea: self-evaluation and the humility to grow
10:17 Accepting feedback as a gift (and removing ego from improvement)
12:40 What to do if you don’t have a coaching manager: retros, recordings, journaling
15:04 A simple feedback framework sellers can use with their manager
20:56 Coaching grizzled/top reps: how to position self-analysis to improve win rates
28:21 Late-stage discipline: don’t replace action with “hoping and praying”
31:06 Staying top of mind without “just checking in”
33:20 Using your team to close: exec notes, CS/engineering support, strategic touches
37:59 Personal manifestos: why action creates momentum (especially mid-January)
40:04 Ryan’s story: early struggle, late payoff, and why consistency wins
46:17 Final takeaway: self-evaluation is transformational for performance

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How to Prospect Like a Human. Susan Unger on Authentic B2B Selling That Wins Meetings

Wed, 28 Jan 2026 21:11:37 +0000

Prospecting hasn’t gotten easier—but it has gotten more human.

In this episode of the My Sales Day podcast, Michael Hess welcomes back Susan Unger, a career prospector who quite literally does this work for a living. Susan is a senior “door opener” at Kopp Consulting, where her sole focus is securing first meetings with C-level decision makers when no prior relationship exists. If anyone understands the emotional grind of cold outreach in today’s market, it’s Susan.

Recorded in mid-January—peak prospecting season—this conversation tackles why so many sellers avoid prospecting, what’s changed post-COVID, and how being prepared actually gives you permission to be more spontaneous, human, and effective. Susan breaks down how phone, email, and voicemail work together to tell a story over time, why vulnerability disarms resistance, and how small shifts—like asking permission or slowing down your delivery—can dramatically improve results.

You’ll also hear why improv classes can sharpen selling skills, how listening to your own recorded calls accelerates growth, and why attitude, energy, and consistency matter more than clever scripts. This is a practical, confidence-building episode for sellers who want to stop dreading prospecting and start owning it.

Featuring: Susan Unger
Host: Michael Hess, My Sales Day

Timestamps

00:01 Welcome back + why this episode matters right now
01:08 Why prospecting feels harder in today’s market
02:32 Kopp Consulting explained: pure cold outreach and “door opening”
03:14 Cold calling C-level execs with no prior relationship
04:36 What changed after COVID—and why clients are more open now
06:23 How Susan hands meetings off and secures the next meeting
08:13 Why locking the follow-up meeting before ending the call matters
09:26 Why sellers avoid prospecting (even when they know better)
10:03 Preparation as the gateway to confidence and authenticity
11:38 Being human on cold calls: vulnerability that works
14:23 Breaking the ice and buying time with empathy
16:03 You can think on your feet—practice makes it natural
18:27 Why improv training improves sales conversations
20:29 Authenticity, self-deprecation, and knowing your limits
24:07 “Show up prepared, then allow your personality”
27:24 Listening to your own calls: self-evaluation that pays off
30:12 Asking permission on cold calls—and why it works
33:31 Gamifying prospecting to beat resistance
36:22 Burst prospecting and building daily momentum
37:55 Why email + voicemail still create impressions
39:22 How managers can coach prospecting through real examples
42:20 Referral-based prospecting: the habit sellers forget
45:39 Motivation, mindset, and confidence rituals that stick
49:14 Quieting the inner voice and just starting
50:11 Final takeaway: better habits, better selling

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Meeting Management for B2B Sellers with Lawrence Horne: Agendas, Storytelling, Trust

Tue, 20 Jan 2026 16:59:30 +0000

In today’s selling environment, you get fewer shots with buyers—and less time when you get them. That’s why meeting management (or better: conversation management) has become a modern sales superpower.

In this episode of the MySalesDay podcast, Michael Hess sits down with Lawrence Horne—joining from the UK countryside—to break down what great sellers do before, during, and after a buyer conversation to earn trust, control momentum, and land the next step.

Lawrence opens with a “Hall of Fame” early-career win: a creative, ambitious ad strategy that required persistence, internal alignment, and the confidence to do something that hadn’t been done before. From there, the conversation gets tactical: agenda-setting, discovery discipline, how to avoid hiding behind decks, and how to read buyer cues when you’re selling over video.

If you’ve ever left a meeting thinking “we talked a lot but learned nothing,” or watched a seller speed-run a slide deck while missing obvious buyer signals, this episode gives you a cleaner framework: set a clear agenda, ask smarter questions early, earn the right to tell the story, and manage the room—especially when there are multiple stakeholders and unclear power dynamics.

To close, Lawrence shares what he does to handle the turbulence of a sales year—the reset, the pressure cycles, and the mindset habits that keep performance steady when the numbers start yelling.

Featuring: Lawrence Horne
Host: Michael Hess, MySalesDay Podcast

Timestamps

00:03 Welcome + Lawrence joins from the UK
01:24 Today’s focus: meeting management and conversation control
02:54 Hall of Fame sale: creativity, competitiveness, and ambition
03:40 The big move: combining dealers into a higher-yield concept
04:37 Crossing lanes? Clarifying internal boundaries and account ownership
05:16 Persistence required: getting 15 stakeholders to agree
06:24 Internal selling and organizational alignment behind the scenes
08:45 Why clustering buyers/sellers increases demand and “yield”
10:39 Why conversation management became the skill Lawrence chose
11:55 Agenda discipline: knowing what the buyer wants to hear
13:45 Why meetings are harder now: fewer buyers, fewer meetings, less time
14:37 Selling over video: why precision matters more than ever
15:05 Stop hiding behind decks: the danger of “get through the slides”
18:59 The 25-minute meeting problem: balancing questions vs. pitching
22:40 Pre-meeting agenda strategy: use the calendar invite to force clarity
39:47 Selling to the top: managing mixed seniority and stakeholder dynamics
42:53 The danger of misreading power in the room
44:03 Handling turbulence: pressure cycles, health, mindset, and habits
46:23 Culture matters: performance gets easier with great people
47:16 The cost of being “the energy person” and why preparation reduces stress
49:07 Closing: better habits equal better selling

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Practical AI Strategies for B2B Sellers and Sales Leaders with Jason Tsai

Tue, 13 Jan 2026 11:00:00 +0000

AI has moved past the “is this real?” phase—and entered the “who’s actually adopting it well?” phase. In this episode of the My Sales Day podcast, Michael Hess sits down with Jason Tsai (joining from London) to break down what AI is actually doing inside modern sales orgs, where teams are still stuck, and how B2B sellers can use AI to sell more—not just produce more “work.”

Jason shares the career path that led him from media planning to digital transformation roles, and ultimately into AI enablement at Pivotal, a growth studio that doesn’t stop at strategy decks—Pivotal embeds with teams to implement change and drive adoption.

From there, the conversation gets practical:

Why AI tools are mature, but adoption is uneven
How sellers go beyond basic “write my email” prompts into scalable prospecting and enrichment
How AI helps verticalize value propositions without breaking brand governance
Where AI is useful for role-play, objection handling, and pressure-testing messaging
The difference between using AI to produce “work slop” vs. using AI to sharpen performance
Why the transformation is only half tools—and mostly human motivation, training, and habits

If you’re a seller, manager, or sales leader trying to figure out what to do next—this is a grounded, non-hype roadmap for using AI to reclaim selling time and raise the bar on how you prepare, message, and execute.

Featuring: Jason Tsai
Host: Michael Hess, MySalesDay Podcast

Timestamps

00:18 Welcome + first MySalesDay episode of 2026
00:40 Jason joins from London: “neither sunny nor dry”
01:23 The mission: tangible AI action items for sellers and leaders
02:10 Jason’s career arc: agency → publisher → Visa → ad tech → AI
04:03 Falling down the AI rabbit hole + the “no time to learn AI” insight
05:49 What Pivotal does: operator-led growth studio, implementation not slides
06:02 Jason’s team: AI enablement, workflow mapping, “robots” that speed up real work
08:32 Agenda: state of AI, skills impacted, adoption resistance
11:04 Where AI is today: beyond experiments, now “uneven adoption”
12:09 Sales AI example: Gong and what call data reveals
13:35 The 30% problem: sellers spend too little time actually selling
15:27 Leveling up prospecting: from ChatGPT searches to scale tools
16:19 Scaling research + enrichment: Clay/Apollo-style workflows
18:05 AI and value proposition: customization at the account/segment level
21:37 Governance: using AI to grade/pressure-test messaging before it ships
25:01 Negotiation prep: scripts, simulations, and objection handling practice
30:28 In-meeting AI: awkward live, powerful for preparation and post-call learning
48:13 Adoption resistance: tools are half the equation—humans are the rest
49:30 How to drive adoption: make it role-specific + prove time savings
51:24 Close: better habits equal better selling

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Complex Sales: Why Nuance Is the Spice of SaaS

Tue, 19 Aug 2025 05:00:00 +0000

In this episode, Grant le Riche, VP of Client Strategy at Eighty Twenty joins me to dive into the mindset required to master the complex sales process. Grant shares how his career evolved from highly transactional sales to a more strategic, consultative approach. We talk about the importance of preparing for every interaction, even when you think it's just a formality, and how he recovered a deal after his boss "junked up" a meeting. Grant also reveals his secrets to building authentic champions and why self-appraisal is a critical skill for any professional seller.

Join us as we discuss:

[2:29] Working with siloed departments and the nuances of complex SaaS sales
[13:45] Why every informal meeting isn’t and champion development
[24:23] If AI is the canary in the coal mine for critical thinking in sales
[37:02] Proactively addressing and shrinking your buyer’s objections

For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player.

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Qualifying Your Buyers: Sharpen Your Invisible Sword to Win More Sales

Tue, 22 Jul 2025 05:00:00 +0000

Qualifying clients is the invisible sword every seller must wield, but too few do so effectively. Penry Price, Founding and Managing Partner at Charcoal Advisors, joins me to explore why qualifying is foundational to successful selling, despite often being underutilized. Penry leans on his experiences at Google, LinkedIn, and other major media entities to highlight how a disciplined approach to qualifying protects precious selling time, uncovers genuine client needs, and ensures that efforts align with opportunities most likely to close. Listen to learn how properly qualifying clients can transform your pipeline, sharpen your strategic focus, and dramatically improve your sales outcomes.

Join us as we discuss:

[1:40] Managing external factors through preparation and persistence
[15:51] Navigating big expectations and why a little paranoia is a good thing
[21:19] How qualifying your clients is your ultimate timesaver
[25:03] Flipping the sense of urgency on its head and the art of brand storytelling

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Don't Just Pitch: A Masterclass in Point of View Selling

Tue, 08 Jul 2025 05:00:00 +0000

Charlie Thomas, Founder of Charlie Thomas Coaching & Consulting, doesn’t focus on pitching harder. Instead, he leans on point of view selling to think bigger. Charlie joins me to share how bold ideas and strategic alignment can transform not just deals, but careers. He recounts the day he closed a multimillion-dollar partnership with Dr. Pepper Snapple by inventing a value-driven offsite on the fly, and how that single act helped multiple clients climb to CMO. From there, he breaks down the mechanics of POV selling, the role of strategic discovery, and why cultivating alignment is key to speed, health, and trust in every sales relationship.

Join us as we discuss:

[2:29] How an authentic point of view creates action and builds trust
[17:33] Why speed and health make up the golden rule of performance — alignment
[25:40] The importance of strategic initiatives and a sense of urgency

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Inside the Recruiter’s Mind: Landing Sales Roles That Fit

Tue, 24 Jun 2025 05:00:00 +0000

Recruiting isn’t just about filling positions but changing lives. Mike Giunta, Managing Director at TalentClimb, joins me to talk about the deeper human side of recruiting, sharing stories of how his careful, ethical approach has built lasting trust and stronger client relationships. From his decision to lose a lucrative placement because of a recruit’s falsified credentials to understanding candidate motivations beyond just career moves, Mike demonstrates why empathy, storytelling, and transparency are essential in recruiting. Listen in to learn how his thoughtful approach to recruiting can positively impact your professional sales reputation and win trust with your long-term clients.

Join us as we discuss:

[4:24] Why transparency is better for long-term ROI over a questionable quick win
[9:34] Emotional transactions in recruiting and the “run to” or “run from” conundrum
[20:17] The juggling act of bragging about yourself versus presenting real value

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Sales Sabotage: Emotionally Resetting After a Busted Deal

Tue, 03 Jun 2025 05:00:00 +0000

To Daryl Faulkner, Account Director at Heritage Werks, “patient tenacity” isn’t just a phrase — it’s a proven strategy. In this episode, Daryl breaks down how he closed a surprising incremental deal with a legacy client known for not having budget. He also shares how attentive listening, long-term relationship building, and asking the right questions set him up to capitalize when a new budget opportunity appeared. We also discuss why rapport matters more than the pitch, how he’s developed presentation skills into a true superpower, and the surprising sales lessons he learned as a paperboy.

Join us as we discuss:

[2:10] Playing the waiting game with a client who has no budget spend
[15:30] Reframing busted deals into potential opportunities
[25:41] When someone sabotages your meeting and firing clients

For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player.

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Human-Centered Selling: Process, Empathy, and a Little Bit of Unreasonable

Tue, 20 May 2025 05:00:00 +0000

Human-centered selling requires more than just closing deals — it means understanding people, showing empathy, and leading with purpose.

In this episode, Doug Weaver, Founder and CEO at Upstream Group, joins me to share the timeless lessons he’s learned from decades of teaching and practicing sales. From a creative career-defining win at Allure Magazine to decades of training top sellers in digital media, connected TV, online audio and ad-tech space, Doug argues for a return to authentic, process-driven selling rooted in curiosity and courage.

Doug and Michael talk about the threat and promise of AI in sales, why the best sellers are “a little bit unreasonable,” and the importance of closing the gap between sales behavior and real human behavior.

Join us as we discuss:

[3:58] Pivoting from overcoming objections to making the human connection
[9:09] Why the sales game has been losing the human touch and the AI conversation
[22:06] Not just taking “yes” for an answer and the current state of sales skills

Check out these resources we mentioned during the podcast:

The Challenger Sale: Taking Control of the Customer Conversation by Matthew Dixon and Brent Adamson

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Why Sales Career Growth Starts with Raising Your Hand

Tue, 06 May 2025 05:00:00 +0000

Sales career growth takes more than just hitting quota. In this episode, Joe Didato — a sales veteran with over 25 years of experience in media, ad tech, and SaaS — breaks down what it really takes to advance and stay relevant. From relationship-driven selling to winning big accounts through custom value alignment, Joe shares practical wisdom that’s helped him thrive across industries. He also reflects on lessons learned the hard way, including a tough interview miss that reshaped his mindset forever.

Join us as we discuss:

[2:12] Selling urgency without being heavy-handed
[9:04] Correcting negative behavior in sales career development
[17:35] Why people won’t just put the time in for preparation
[20:27] Transitioning from traditional sales to SaaS and essential skills

Check out these resources we mentioned during the podcast:

RepVue

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Be Assertive: The Hardest Learned Skill in Sales Relationships

Tue, 22 Apr 2025 05:00:00 +0000

Strategic sales relationships take time — and Erin Frey knows the payoff. As Senior Account Executive at Nexxen, Erin shares how she transitioned from the buy side to becoming a trusted, long-term partner to clients.

In this episode, Erin dives into the power of empathy and relationship-building in a fast-moving and unpredictable sales world. We discuss how to balance transactional and strategic selling, why courage matters more than confidence, and the daily grind of building structure in an unstructured sales day.

Join us as we discuss:

[2:13] Why sellers shouldn’t be afraid to dig deeper into their client relationships
[7:57] The biggest mindset shift after jumping into sales from the buyer’s side
[12:11] Confronting and correcting passive sales behavior
[18:07] How to get your virtual sales call participants to turn on the camera

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Selling a Business (Twice!): Lessons in Sales and Entrepreneurship

Tue, 08 Apr 2025 05:00:00 +0000

Sales is more than just closing deals — it’s about discipline, evolution, and knowing when to adapt.

Nik Kontoulas, Managing Director ANZ at Seedtag and CEO and Founder of JustEggs, joins me to share his journey from an ambitious young seller to launching and selling a business — twice. Nik unpacks the evolution of the sales pitch, explaining why the best sellers are those who anticipate market changes before anyone else. He also discusses the power of discipline, why being the first in the office still matters, and how to win deals without relying on a pitch deck.

If you're a seller looking for an edge, Nik’s battle-tested insights will give you the confidence and strategy to take your career to the next level.

Join us as we discuss:

[4:04] The evolution of the sales pitch process as an entrepreneur
[12:53] Why you shouldn’t be afraid to hound leads for their business
[21:08] Getting your sales team to buy-in on leveling up their skills

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Sales Storytelling: Making the Buyer the Hero

Tue, 25 Mar 2025 05:00:00 +0000

What are the ingredients to a great sales pitch?

According to Matt Rosenberg, Principal Consultant at First Chair Marketing, they’re storytelling, collaboration, knowing how to find and use sales enablement help.

Matt shares insights with me from his experience leading sales solutions teams and working hand-in-hand with sellers as well as consulting for businesses with widely different sales cultures.

He discusses why team selling creates better outcomes, how sales enablement teams should (and shouldn’t) frame proposals, and why the best salespeople make the buyer the hero of the story.

From practical strategies to get enablement teams on your side to the importance of excitement and confidence in a sales pitch, this conversation is packed with insights every B2B seller needs.

Join us as we discuss:

[3:32] How to build your sales storytelling round your buyer
[9:49] Where sellers often struggle in their storytelling scripts
[20:14] Crafting a custom narrative that gets your buyer talking

For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player.

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Closing Big Accounts Through Incremental Selling

Tue, 11 Mar 2025 05:00:00 +0000

Big sales typically don’t happen overnight — momentum builds in increments.

Stuart Prentice, Senior Account Executive at Nexxen, joins me to break down how resilience in sales isn’t about grinding endlessly but about recognizing and capitalizing on small wins. We discuss the power of incremental selling and keeping deals alive through consistent engagement, adding value before contracts are signed, and strategically re-igniting stalled conversations.

If you’ve ever felt stuck in a long sales cycle, this episode will give you a new perspective on how patience, persistence, and well-timed nudges lead to big wins.

Join us as we discuss:

[2:27] How Stu proved his value over a 3-year deal build-up
[11:59] Maintaining momentum in the day-to-day sales grind
[16:25] Getting out of a “sales slump” and knowing when to hit pause

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The Seller's Credo: Understand Before Being Understood

Tue, 04 Feb 2025 06:00:00 +0000

In this compelling episode, Steve Loguidice, CEO and founder of Varisa Strategic Advisers, shares hard-earned lessons from his 22 years in the industry.

Steve talks about how he turned a long-shot pitch into a groundbreaking deal with MTV during his time at BuzzFeed. By focusing on the client’s needs and aligning with their long-term goals, Steve was able to create a campaign so effective it became the blueprint for future collaborations. We also discuss the importance of asking the right questions, such as “What do you need for your money?” — a blunt perspective that transforms conversations from transactional to strategic.

With practical advice on leveraging data, building trust, and understanding buyer motivations, this episode is packed with actionable insights for professionals aiming to elevate their strategic sales game.

Join us as we discuss:

[2:50] Beavis and Butthead and the psychology of salesmanship
[13:05] What it means to understand before being understood
[20:08] Intentional self-improvement and the value of role-playing
[24:57] The importance of tracking your personal sales KPIs

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Chosen Suffering: Make Sales Feel Easy Through Hard Life Habits

Tue, 28 Jan 2025 06:00:00 +0000

Stephen Clifford (Cliff), Managing Director of East Coast Client Partnerships at Infillion, thinks a lot of sales professionals spend too much time behind a screen — and not enough of it getting in front of their clients.

Cliff shares how creative outreach (like a game of pickleball) and empathy-driven approaches can help sellers connect with even the toughest decision-makers. He also discusses the importance of asking tough questions, managing rejection, and balancing healthy paranoia, grace, and humility in a high-stakes career.

Tune in for practical advice and powerful anecdotes from a sales veteran who knows how to turn connections into long-term partnerships.

Join us as we discuss:

[4:00] Building a long-term relationship by getting whipped in pickleball
[14:37] How being too nice can backfire in sales meetings
[19:24] Approaching sales relationships with a pizza delivery mindset
[26:40] Why Cliff does hard activities to make sales feel easier

Check out these resources we mentioned during the podcast:

Forgotten Wisdom Books

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Feel Empowered By “No”: Pushing Through Barriers and Sales Burnout

Tue, 21 Jan 2025 06:00:00 +0000

Resilience defines every great salesperson, and Nena Slifer, Vice President of Healthcare Strategic Partnerships at iHeartMedia, has embodied it in every step of her career.

From overcoming the challenges of being a young, single mother to mastering enterprise-level sales, Nena’s journey is a testament to grit, thoughtfulness, and strategic vision. She shares how she turned a rejected pitch into a multi-season podcast, the delicate balancing act of managing relationships between clients and agencies, and her proven strategies for combating sales burnout while staying motivated.

Nena’s story offers invaluable lessons and inspiration for surviving and thriving in the face of today’s turbulent sales headwinds.

Join us as we discuss:

[4:06] Establishing a sales career as a young, single mother
[7:35] The delicate dance between pleasing clients and your boss
[15:40] Making the most of your time during the sales doldrums
[28:01] Pushing through on the account when a buyer doesn’t like you

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Why Ownership Outshines C-Suite Oversight in Closing Deals

Tue, 14 Jan 2025 06:00:00 +0000

Ownership isn’t just a leadership buzzword — for Lindsey Dobbs, it’s her secret sauce for sales success.

The Senior Director of Sales at Nexxen joins me to share how embracing ownership at every step, from preparation to delivery, has defined her career. Whether she’s building strategic partnerships or probing for insights, Lindsey’s approach exemplifies how taking charge can differentiate a sales professional in a crowded field.

This episode dives into Lindsey’s top three skills for daily success, how preparation amplifies results, and why you should go into every sales deal with an ownership mindset.

Join us as we discuss:

[1:26] How taking ownership of your work can lead to big opportunities
[11:57] Sales traits versus skills and leaning on your core motivations
[21:55] Key advice for sellers who might not be naturally curious

Check out these resources we mentioned during the podcast:

The Road Back to You by Ian Morgan Cron and Suzanne Stabile

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The Hustler’s Playbook: The Four P’s of Strategic Sales Skills

Tue, 07 Jan 2025 06:00:00 +0000

Katie Barrett knows what it takes to win in sales — a mix of strategy, belief, and relentless preparation.

The Head of Strategic Sales at LG Ad Solutions has spent two decades honing her craft, from career-defining wins to perfecting the art of internal and external partnerships. Katie shares why belief in yourself is the foundation of every successful sale, why preparation is the ultimate sales advantage, and why savvy sellers need to be thorough when reading their contracts and not leaving it up to their manager.

Whether you're closing deals or building relationships, Katie’s insights will inspire you to elevate your game.

Join us as we discuss:

[3:01] The underlying importance of confidence when pitching yourself
[9:25] A love for sales contracts and their evolution in the Digital Age
[16:43] Why the greats make preparation their number one priority
[23:15] Stepping back and resetting when the sales life gets tough

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Forcing Your Tech-Dominant Org to Buy In on Selling Strategies

Tue, 10 Dec 2024 06:00:00 +0000

Internal selling can be just as critical as closing external deals. That’s why I invited Andrew Furman, General Manager - North America at Outbrain, to discuss the discipline of selling ideas within your own organization.

From dealing with hierarchical roadblocks to turning skeptics into champions, Andrew shares his story of breaking into new sales verticals at Outbrain.

Discover actionable insights on emotional intelligence, strategic leadership, and finding the right champions to bring your vision to life. Whether you’re a sales rookie or a seasoned pro, this conversation will leave you rethinking the dynamics of internal collaboration and influence.

Join us as we discuss:

[2:29] A lesson on digging deeper and not taking deals at face value
[14:19] Identifying the right champion in your sales discovery process
[21:22] The importance of codifying your sales team’s culture

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How Today’s Top Sellers Master Client Loyalty

Tue, 03 Dec 2024 06:00:00 +0000

What separates a good sales professional from a great one? It starts with cultivating good relationships so your sales conversations can go deeper.

Stephanie Reustle, VP of East Coast Sales at Digital Remedy, joins me to share her tried-and-true methods for maximizing client relationships. From earning trust to turning customers into long-term advocates, Stephanie reveals the strategies that make her one of the most effective sales leaders in the industry.

Whether you're a seasoned seller or fresh off the mean streets, this conversation will change the way you think about client connections.

Join us as we discuss:

[2:33] Winning a $20M deal by cultivating “sticky” relationships

[11:05] Probing your clients’ social media footprint to try and learn how they think

[22:35] When the client “unsubscribes” to your perfectly crafted email

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The Storytelling Edge: From Conversations to Conversions

Tue, 26 Nov 2024 06:00:00 +0000

Forget boring pitches — Paul McGhee, Revenue Enablement Director at Clari, knows that storytelling is the secret weapon every sales pro needs.

In this episode, Paul unpacks how killer narratives can turn lukewarm leads into loyal customers. He’s got the blueprint for keeping it simple, solving real problems, and getting buyers to open up.

Plus, he shares why focusing on your performance — not the scoreboard — will keep you sane and successful in today’s cutthroat market. Tune in if you’re ready to ditch the stale scripts and sell with swagger.

Join us as we discuss:

[2:56] How to open a new big market by closing a small $70k deal
[7:21] The different sizes and shapes of sales stories
[18:11] Why selling success must include a heavy dose of the right kind of roleplaying

Check out these resources we mentioned during the podcast:

Zenarate

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Coffee Over Cold Calls: Why Relationship-Based Selling Wins

Tue, 12 Nov 2024 06:00:00 +0000

Paul Cassar, Head of Enterprise Partnerships at DanAds, joins me to share why relationship-based selling isn’t just a strategy — it’s the secret weapon many sales professionals take for granted.

We share stories that blend humor, hard lessons, and high stakes, showing how listening and authentic engagement can turn casual meetings into massive deals.

From an embarrassing misstep that ended with public criticism to a career-making win that began with a simple chat over coffee, Paul and I unpack why playing it safe won’t cut it in today’s sales world.

Join us as we discuss:

[4:24] When a “smooth” meeting turns into a humiliating disaster
[13:10] Why relationships are your greatest asset in the long-game
[20:34] Finding the courage to get personal and ask tough questions

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“And Then, I Shut Up”: Learning to Sell With Your Mouth Closed

Tue, 29 Oct 2024 05:00:00 +0000

Diligence and a heavy focus on input — that’s the mindset that has driven Ryan Picchini, VP of Channels and GTM Strategy at dotCMS, to close some of the largest deals in the competitive Martech space.

Ryan tells me how his meticulous preparation has helped him succeed against even the biggest competitors.

From a multi-million dollar deal with Edward Jones to the importance of team selling, Ryan offers valuable insights for sales professionals looking to sharpen their skills in a crowded market.

Join us as we discuss:

[1:04] Getting back to sales basics and focusing on inputs
[12:54] Team selling and persona matching
[19:43] Why your professional network is your net worth

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Strategic Selling: Turn Challenging Buyers into Long-Term Clients

Tue, 22 Oct 2024 05:00:00 +0000

For sales leaders trying to stay afloat in tough markets, it’s not just about what you sell but how you engage reluctant clients.

Leah Corselli, VP of US West at The Independent, has spent over two decades building relationships with hard-to-reach buyers. Leah joined me to share the strategies that helped her turn challenging clients into long-term partners and close groundbreaking deals, including a multi-picture deal with Universal Pictures.

Learn how she leverages strategic selling by mobilizing teams and maintaining clear, consistent communication with both clients and colleagues.

Join us as we discuss:

[6:20] Closing a massive digital ad deal in the early days of the Internet
[13:40] How to get difficult buyers to work with you
[23:27] Why you can’t take the sales life personally

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When in Rome: Sales Resilience in a Pit of Lions

Tue, 15 Oct 2024 05:00:00 +0000

Kevin Weafer, President and CEO of Spinar America, joins me to discuss strategies for staying grounded in the challenging world of sales.

Drawing from decades of global sales experience and unique methods of balancing emotional resilience with tactical execution, our conversation covers how to navigate the modern sales landscape, particularly during turbulent times.

From maintaining personal wellness to projecting the future of AI technology, Kevin’s insights are a must-listen for high-powered sales professionals looking to sharpen their skills and thrive amidst uncertainty.

Join us as we discuss:

[00:50] Why self-care is critical in the sales long game
[13:36] The struggle of keeping both clients and management happy
[23:12] Why doing homework is one of the hardest sales skills to master

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Internal Influence: The Formula for Successful Sales Starts Inside

Tue, 08 Oct 2024 05:00:00 +0000

Seasoned sales veteran John Irvine, Director of Consumer Journeys at Propel Advantage, joins me to talk about the role your internal influence can play in negotiations and long-term client relationships.

John recounts how he successfully pitched a challenging idea to a whale client, turning a skeptical buyer into a supporter through data-driven arguments and competitive selling. We also chat about the importance of internal collaboration with your management team and how treating colleagues with respect can lead to wins.

Tune in to hear John's valuable advice on sales negotiations and building strong client relationships.

Join us as we discuss:

[1:12] Using data and competitive selling to overcome objections
[9:19] How internal influence bears collaborative results
[20:52] Doing your homework and making the client the hero

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Sweet Emotion: Win Trust and Business with Relentless Empathy

Tue, 01 Oct 2024 05:00:00 +0000

Susan Unger, Director of Sales at Informa, joins me to unpack value selling and how showing vulnerability can positively influence your relationships with your customers.

With over 25 years of selling experience, Susan shares some of her defining career moments that highlight the impact of consistency and empathy in sales.

Learn how focusing on the value narrative can transform your sales strategy and lead to significant wins.

Join us as we discuss:

[00:50] Why you should always steer the conversation back to value
[9:47] Mirroring conversations and empathetic listening
[22:59] When a sales day goes bad and conflict resolution

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Human Speak Your Value Prop: Stop Treating People Like Dollar Signs

Tue, 24 Sep 2024 05:00:00 +0000

Brian McFarland, Sales Director for Key Accounts at Ogury, shares the core principle behind his three decades of selling of successfully communicating his value proposition — trust.

Brian discusses how he managed a multi-million dollar account by focusing on listening and understanding his clients' needs and how this superpower of gaining trust quickly and deeply has driven his sales career.

Tune in to hear how treating your buyers like people — instead of dollar signs — can transform your sales strategy and lead to long-term success.

Join us as we discuss:

[1:00] Snagging a $10M account by finding the right decision-makers
[11:23] Consistent human-centric messaging in your value proposition
[18:50] Why less is more and respecting the silence

For more My Sales Day, subscribe to the inspiring MySalesDay newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player.

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Sales Grit: Asking Hard Questions for Valuable Buyer Insights

Tue, 17 Sep 2024 05:00:00 +0000

Jeff Zito, Senior VP of Sales at Nexxen, joins me to talk about his biggest payoffs from perseverance over his 15-year sales career.

Nobody in our industry wants to hear the word “no,” but Jeff and I unpack how every objection is an opportunity to ask hard questions and learn from our mistakes.

Tune in to hear how the right attitude and effort can help you turn around your sales fighting position.

Join us as we discuss:

[6:55] Why asking the tough questions is a sales superpower
[13:03] Attitude, effort, and overcoming objections
[21:03] Turbulence and gyration in today’s sales life

For more My Sales Day, subscribe to the inspiring MySalesDay newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player.

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The Sales Relationship: Understand What’s Important to Your Buyers

Tue, 10 Sep 2024 05:00:00 +0000

For the premiere episode of My Sales Day, I’m excited to talk with Darin Leach, Growth Strategy Consultant at MadTech.

Darin’s participated in several blockbuster deals during his remarkable sales career, including a digital marketing contract with the Subway restaurant chain.

Tune in to hear our conversation on the importance of time management in the sales funnel, understanding what really matters to your clients, and the art of walking away from a deal.

Join us as we discuss:

[8:06] How an early career win informs Darin’s sales approach today
[19:01] Why good time management is your sales funnel’s best friend
[27:42] When it’s time to leave a deal on the table

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Welcome to My Sales Day...

Tue, 13 Aug 2024 15:37:35 +0000

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

I’m Michael Hess, Founder and Chief Seller Advocate of “My Sales Day”, and it's my job to make “the sales life” "less messy" for you...and of course, to help you excel and perform at your peak abilities.

My goal is to make your time here educational, inspirational, and actionable. And yeah, entertaining too…sales doesn’t have to be boring! Selling is fun too, so let’s have some of that here as well.

You'll get skill ideas, action items, and hugs.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

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