OhHello with Jeremy Bloom

By Jeremy Bloom

OhHello with Jeremy Bloom is a no-BS career mentorship and leadership podcast for people who want to get better at what they do — and enjoy the process.

Hosted by Jeremy Bloom, founder of OhHello.a... more

Download on the App Store

Download on the App Store

Get it on Google Play

FAQs about OhHello with Jeremy Bloom:

How many episodes does OhHello with Jeremy Bloom have?

The podcast currently has 127 episodes available.

OhHello with Jeremy Bloom episodes:

May 05, 2026OhHello Ep.123 The “CMO Whisperer” Reveals What Marketing Leaders Won’t Say Publicly with Steve Olenski
Steve Olenski, Founder of The CMO Whisperer Advisory, joins Jeremy Bloom to share what CMOs really think behind closed doors on credibility, AI pressure, career growth, and why marketing is still misunderstood in the C-suite.

Takeaways
CMOs struggle with credibility, not creativity

Marketing is still undervalued in the C-suite

AI is increasing pressure on marketing teams

Alignment matters more than “great work.”

Everyone thinks they understand marketing

The best leaders embrace humility and empathy

Authenticity is critical for long-term success

Career growth comes from understanding business impact

Relationships are built with genuine intent

Paying it forward is a leadership responsibility

Chapters
00:00 Intro & Meeting the “CMO Whisperer”
01:00 The Origin Story at Forbes
04:10 What CMOs Really Say Behind Closed Doors
05:45 What the Industry Gets Wrong About Marketing
07:00 Why CMOs Have the Shortest Tenure in the C-Suite
08:25 What Marketers and Executives Don’t Understand
09:15 “Everyone Thinks They Know Marketing”
11:00 Breaking Down Silos in the C-Suite
11:25 Building Real Relationships & Access
13:45 What Keeps CMOs Up at Night
15:20 Mentorship & Career Growth
17:25 Lessons from Great Leaders
19:25 Hiring Smart People & Letting Them Lead
21:10 Common Career Mistakes
23:50 Advice for Younger Professionals
24:30 Final Thoughts: The Human Side of Business
...more
23min
April 21, 2026OhHello Ep. 122 Why Salespeople Burn Out And How to Actually Succeed with Dr. Deepak Bhootra
Dr. Deepak Bhootra, Chief Executive Officer of Jabulani Consulting, shares hard truths about sales and leadership, and why so many professionals struggle despite all the tools, training, and technology available today.

Takeaways
Sales success is less about adding skills and more about removing internal noise

Mindset and attitude matter more than technique

Many salespeople burn out not from failure, but from pressure and emotional strain

Leaders often focus on metrics but ignore the human behind performance

Coaching people is more effective than managing numbers

Asking for help is difficult because of fear and perceived expectations

Self-compassion is critical for long-term growth and resilience

Career growth often requires having difficult, avoided conversations

Chapters
00:00 Introduction to Dr. Deepak Bhootra
01:20 Background, purpose, and personal journey
03:14 What most people get wrong about sales
04:22 Why salespeople burn out early
05:45 The importance of leading indicators
06:06 Why salespeople get stuck
07:39 Why people struggle to ask for help
09:00 Burnout, mental health, and career shifts
11:01 The power of coaching and mentorship
11:53 What leaders get wrong in enablement
13:29 Coaching people vs managing numbers
13:53 Mentors that shaped Deepak’s career
16:33 Advice for those feeling stuck
18:27 Final thoughts and closing
...more
19min
April 14, 2026OhHello Ep. 121 From Finance to Community Builder: Amelia Tran on Grit, Mentorship & Career Growth
Amelia Tran, General Manager at Marketecture Media and Founder, Asteria Collective, shares her journey from finance to marketing, the power of community, and how grit, mentorship, and relationships shaped her career. Discover actionable insights on networking, trust-building, and navigating career growth.

Takeaways
Relationships should be built before asking for help

Action matters more than perfection

Consistency builds trust over time

Mentorship can completely change your career path

Grit comes from turning nothing into something

Growth requires stepping outside your comfort zone

Feedback helps you understand your true strengths

Strong relationships make asking for help easier

Chapters
00:15 Introduction and welcome
00:52 Amelia shares who she is and what she does
01:22 Running communities and building opportunities
02:23 Starting in finance and career pivot
03:00 Mentorship that changed her path
04:25 Early career and agency experience
06:24 Where her grit comes from
10:25 Building trust and credibility
13:24 Realizing she could operate at a higher level
16:20 Key mentors and influence
17:58 How to ask for help effectively
20:12 How high performers handle friction
21:45 Advice for when you feel stuck
23:02 Final thoughts on relationships and growth
...more
23min
March 31, 2026OhHello Ep. 120 Brad Jaehn on Mentorship, Leadership, and the Future of Work
Brad Jaehn shares his recent experience of being unexpectedly terminated over mentoring activities, explores the importance of human connection in leadership, and discusses the evolving role of AI and distributed teams in the workplace.

Takeaways:
The importance of mentorship and human connection in leadership

The impact of organizational culture on employee development

The role of AI in the future of work and human guidance

Challenges and opportunities of distributed teams

The significance of asking for help and mentorship in career growth

Chapters
00:00 Introduction and Personal Connection
01:03 Brad Jaehn's Background and Career Highlights
02:05 Recent Termination Over Mentoring Activities
03:25 Reflections on the Impact of Mentoring and Giving Back
06:18 Organizational Investment in People and Leadership Development
07:56 The ROI of Employee Development and Mentorship
09:18 Mentoring as a Leadership Skill and Organizational Priority
09:52 Mentors Who Influenced Brad’s Career
11:20 The Role of Human Guidance in the Age of AI
13:34 Leading Distributed Teams and External Perspectives
15:02 The Future of Leadership and External Help
15:55 Advice for Aspiring Leaders and Mentorship
16:46 Closing Remarks and Final Thoughts
...more
17min
March 24, 2026OhHello Ep. 119 On Confidence, Career Pivots & Choosing Movement Over Comfort
Jackelyn Keller, a marketing leader, strategist, and educator—and Founder of Jackwell Partners, a marketing consultancy—shares her journey from sales assistant to CMO and what it taught her about trusting your instincts.

Known for translating complex technology into clear, actionable strategy, she explores career pivots, building confidence without certainty, and why mentorship and relationships often matter more than resumes.
Takeaways
Confidence isn’t about having all the answers–it’s trusting that you’ll figure it out.

Career growth comes from trying new things rather than staying where you’re comfortable.

Relationships often matter more than what’s on your resume.

Mentorship works best when it’s rooted in empathy and active listening.

Taking care of yourself shapes how you show up at work and in life.

Chapters
00:00 Introduction to Jackelyn Keller and her background
02:30 Building a career across marketing, teaching, and entrepreneurship
06:10 Knowing when to push through versus when to pivot
07:45 Taking risks before feeling ready
10:00 Redefining confidence as self-trust
11:40 Overcoming fear of public speaking through teaching
14:15 Mentors who shaped her career
16:20 What makes a great mentor
17:20 Why leaders struggle to ask for help
18:20 Managing self-doubt and personal pressure
20:00 The importance of outside perspectives
22:20 Advice for early-career professionals
23:15 The value of mentorship and community
...more
23min
March 17, 2026OhHello Ep. 118 Jason Loehr, Data & AI Advisor: How Empathy, Curiosity & Data Drive Better Leadership
Jason Loehr, a data and AI advisor with experience across companies like Camping World and Brown-Forman, joins Jeremy Bloom to discuss how leaders can combine technology, empathy, and critical thinking to navigate digital transformation. They explore Jason’s early experience launching one of the first online catalogs, how consumer-first thinking shaped his career, and why AI should empower people rather than replace them. Jason also shares insights on leadership, curiosity, and how organizations can use data and learning agendas to make better decisions.

Takeaways
Early digital innovation showed Jason that understanding customer lifetime value can reshape how companies view new technology.

Successful digital transformation happens when organizations prioritize consumer experience over internal convenience.

AI should free up human time for deeper critical thinking rather than replace human roles.

Empathy and creative friction are essential for solving complex problems and building better ideas.

Organizations make better decisions when they focus on the questions they need answered before gathering data.

Democratizing data helps teams collaborate and solve problems faster across the organization.

Leaders should automate predictable work, elevate human judgment, and optimize decision velocity.

Technology itself is not the disruptor but the tool that enables meaningful disruption.

Chapters
00:00 Jeremy welcomes Jason and introduces his background in digital transformation and marketing.
01:00 Jason shares his career journey from early e-commerce to working with major global brands.
03:30 Why consumer-centric thinking should guide technology and digital decisions.
05:30 Leadership traits, including curiosity, relationship building, and humility.
08:30 How AI and empathy work together in the future of work.
10:20 Using data and learning agendas to improve decision making.
13:00 A leadership framework automates predictable tasks, elevates human insight, and optimizes velocity.
14:00 The mentors and relationships that shaped Jason’s career.
16:00 Why leaders must stay intentional when adopting new technologies.
...more
18min
March 03, 2026OhHello Ep. 117 From Hustle to Human-Centered Leadership: Jay Wolff on Letting Go and Lifting Others
In this engaging conversation, Jeremy Bloom and Jay Wolff explore the intricacies of leadership, mentorship, and the importance of human connection in the digital advertising industry. Jay shares his journey from the early days of digital advertising to his current role, emphasizing the significance of empowering others and building meaningful relationships. The discussion highlights the value of networking, the role of mentorship, and practical advice for motivating teams and fostering a supportive work environment.

Takeaways
Leadership is about connecting people and empowering them.

The journey to leadership involves learning through experience.

Mentorship can come from various sources, including family and colleagues.

Networking should be genuine and reciprocal, not transactional.

Small gestures can have a significant impact on relationships.

Understanding individual motivations is key to effective leadership.

Creating a supportive environment fosters psychological safety.

Involvement in local organizations can enhance career growth.

Building a personal brand is essential in today's professional landscape.

Empowering others leads to a more successful and cohesive team.

Chapters
00:00 Introduction and Background
02:42 Defining Leadership and Team Building
05:40 The Journey to Leadership
08:41 Mentorship and Influences
11:44 The Importance of Networking
14:21 Motivating and Empowering Teams
17:31 Final Thoughts and Advice
...more
25min
February 10, 2026OhHello Ep. 116 Ajinkya “Jinx” Joglekar, ex-CMO Dish & Sling, on mentorship and curiosity
Ajinkya “Jinx” Joglekar joins Jeremy Bloom to share what he learned leading marketing at Dish and Sling, why he decided to take the leap into consulting after 20+ years in corporate, and how curiosity became the skill that helped him “punch above his weight” early in his career.
They also dig into what real mentorship looks like, how leaders can build a culture of learning across teams, and why great advertising is not just creative and media but also the sales experience.

Takeaways
Your corporate career can be the venture capital that funds your future risk-taking.

Curiosity lets you lead and influence even before you have a title or direct reports.

Great advertising only works when creative, media, and the sales experience are connected.

Leaders build learning cultures by meeting every level of the team and making collaboration unavoidable.

Mentorship programs work best when they are supported from the top but driven organically from the ground.

Chapters
00:00 Jinx introduces himself and his background leading marketing at Dish and Sling.
03:05 Why he left the CMO seat to bet on himself and start consulting.
06:40 The mentor who gave him his first real marketing start and taught him scrappy fundamentals.
12:10 The moment he realized curiosity is a career advantage that helps you punch above your weight.
14:40 How to build a culture of learning through one-on-ones and cross-team collaboration.
18:10 Advice for emerging marketers and sellers: don’t stay in your lane and use your network.
20:05 How organizations can create mentorship programs that work without feeling forced.
...more
26min
February 03, 2026OhHello Ep. 115: Scott Hess on Leadership, Joy at Work, and Creating Opportunity Through Mentorship
Jeremy Bloom and Scott Hess, Chief Marketing Officer of Starcom and Chief Marketing Officer of Publicis Media, discuss the significance of the Chicago Advertising Federation's Career Day, the importance of mentorship and networking in the advertising industry, and personal experiences that shaped their careers. They reflect on the joy of working in advertising and the opportunities available for young professionals entering the field.
Takeaways
Scott Hess is the Chief Work Officer of Publicis Media.

The Chicago Advertising Federation's Career Day is crucial for networking.

Mentorship can significantly impact career paths in advertising.

Career Day demystifies the advertising industry for young people.

Networking events provide access to industry leaders and opportunities.

Scott's son found joy in advertising after initially pursuing engineering.

The advertising industry offers diverse career paths and opportunities.

Personal connections can lead to job opportunities and mentorship.

The excitement of young professionals can reinvigorate seasoned veterans.

Chicago's winter can be a downside, but the city has much to offer.

Chapters
00:00 Introduction and Background
02:43 The Importance of Career Day
05:37 Mentorship and Networking in Advertising
08:50 Personal Experiences and Career Paths
11:38 The Joy of Working in Advertising
14:37 Conclusion and Upcoming Events
...more
16min
January 27, 2026OhHello Ep. 114: Heather Macaulay on Building MadConnect, Leadership, and Solving Ad Tech Complexity
Heather Macaulay, President of MadConnect, joins Jeremy Bloom to talk about simplifying complexity in ad tech, making career decisions across different life seasons, and why the best leaders focus on problem solving, listening, and connecting people behind the scenes.

Takeaways
Heather Macaulay is the president of MadConnect.

MadConnect automates connectivity in the advertising ecosystem.

Presenting a clear message is crucial for success.

Entrepreneurship requires taking risks and trusting oneself.

Sales should focus on problem-solving rather than transactions.

Mentorship plays a vital role in career development.

Balancing career and family requires conscious decisions.

Building a personal brand involves genuine connections.

Listening is key to effective mentorship.

Your network is essential for success in any industry.

Chapters
00:00 Introduction to Heather Macaulay
02:41 Understanding MadConnect and Its Role
05:52 The Journey to Entrepreneurship
08:33 Sales Strategies and Problem Solving
11:38 Mentorship and Guidance
14:37 Balancing Career and Family Life
17:20 Building Trust and Personal Brand
20:39 Parting Words and Industry Insights
...more
23min

FAQs about OhHello with Jeremy Bloom:

How many episodes does OhHello with Jeremy Bloom have?

The podcast currently has 127 episodes available.