What it IS:
Honest conversations about leadership, growth, and decision-making
Space to talk about how definitions of success evolve over time
A thoughtful audience of founders and executives leading B2B organizations
Strategy, people, operations, and resilience — not highlight reels
What it is NOT:
A promotional interview
A sales pitch for your product or service
A rapid-fire “tell us your origin story” show
A hidden sales pitch to you for our services
We encourage you to apply to be interviewed if you are:
A founder, CEO, or senior leader
Leading a B2B organization (or serving B2B at scale)
Past the early hustle stage
Willing to speak candidly about challenges and tradeoffs
Reflective about leadership, not performative
Interested in contributing insight, not just exposure
But, you're probably not a fit if:
You’re primarily looking to promote an offer
Your work is consumer-focused or influencer-driven
You’re early-stage and still figuring out your direction
You want scripted questions or talking points
YOU DELIGHT IN THOUGHTFUL REFLECTION
We’re drawn to leaders who think deeply about their decisions — not just what worked, but why it worked, what it cost, and how it changed them. The most meaningful conversations come from people who’ve taken time to reflect on their leadership journey, not just narrate it.
YOU VALUE INTEGRITY OVER IMAGE
This podcast values honesty over performance. We’re not here for polished origin stories or highlight reels. We’re looking for leaders who are willing to talk about real tradeoffs, missteps, and second-order effects — because that’s where the learning lives.
YOU'VE GOT A COMMITMENT TO CLARITY
We believe clarity is a leadership responsibility. Strong guests care about aligning people, priorities, and decisions as their organizations grow. They value plain language over jargon and are thoughtful about how success is defined, measured, and communicated inside their organization.
YOU WANT TO EMPOWER OTHER LEADERS
Measures of Success is a space for leaders who want to give useful and practical insights to others navigating similar challenges. Guests come with the intention to contribute lessons learned, perspective, and lived experience — not to promote, pitch, or posture..
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Jennifer Todd is a CPA and Connected Strategy Advisor who helps founders and leadership teams clarify what success actually means — and align their organizations around it.
A founder for 21 years, Jennifer brings nearly three decades of experience working inside growing organizations and a deep respect for the realities of leadership as complexity increases.
Measures of Success creates space for honest conversations about how definitions of success evolve, where growth creates friction, and what it takes to build organizations that truly support the people leading them.

Founder-Lived Perspective
With 21 years as a founder, Jennifer understands leadership from the inside — including the isolation, tradeoffs, and responsibility that come with growth.
Clarity Over Complexity
She helps leaders cut through noise and jargon to define success in plain language that people across the organization can actually act on.
Connected Strategy Thinking
Jennifer specializes in bridging the gaps between vision, numbers, people, and execution so strategy becomes coherent, not theoretical.
Respect for Real-World Constraints
Her approach honors the lived realities of mid-market organizations — limited time, competing priorities, and the human dynamics that shape results.
Frequently Asked Questions
If you think you're a good fit, you probably are! Please apply. We'll review your application and, if we think you're a good fit, we'll reach out to schedule a 15-minute chat to get to know you better. Your application is not a commitment; it's just your signal to us that you've got a perspective you think will help our audience of founders and business leaders.
Leading is often a lonely job. Other business leaders are very interested in hearing about the successes and struggles that other leaders go through on their entrepreneurial journey. Listeners tune in to explore questions like:
How has your definition of success changed as your organization has grown?
Where did growth create friction you didn’t anticipate?
What decisions had the most impact on your success and where you are today?
How do you align people, priorities, and performance as complexity increases?
What would you do differently with the benefit of hindsight?
If your application is approved, we'll reach out by email with a calendar link to schedule a 15-minute follow up "right-fit" call. Once we agree that its a fit, we'll send another calendar link to our recording studio. You'll be required to sign a podcast guest agreement.
You can expect:
Jennifer to draft a compelling intro for you
45 –60 minute recorded conversation
Pre-call context so the conversation flows naturally
No prep deck, no scripts
Edited professionally and shared with you upon release
Clips provided for optional sharing with your audience
Measures of Success is created to empower small business founders with insights they rarely have access to — the kinds of lessons, tradeoffs, and second-order decisions that are usually only shared behind closed doors.
It also serves B2B leaders in mid-market professional services organizations who are navigating the complexity that comes with growth: aligning people, priorities, and performance as the organization scales.
Across both audiences, the podcast is for leaders who want to move beyond surface-level advice and engage with honest conversations about how success is defined, how it evolves, and what it truly takes to build organizations that work — not just on paper, but in real life.
This is a brand new podcast (we began production on December 9, 2025). We will be publishing our podcast on all the major podcast channels, on LinkedIn, YouTube, and our Jennifer Todd's companies' websites. Listen now.


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