Leading Your Life Coaching

I empower people to live their best lives every day and to achieve their greatest career and life aspirations! I currently coach dozens of high-achieving professionals and entrepreneurs in creating the life of their dreams.

FOCUS AREAS INCLUDE:
▶️ Career Advancement
▶️ Personal Effectiveness - Reducing Stress
▶️ Leadership, Communication and Influence
▶️ Strengthening Relationships
▶️ People Management, Team Development and Coaching
▶️ Wealth and Financial Freedom
▶️ Career Transitions

I have been coaching people inside and outside of the workplace for well over a decade, recently departing the corporate world to focus on my passion full time. I have obtained a Level 2 (PCC) certification from the International Coaching Federation (ICF).

Executive Leadership Trainer & Coach (PCC Certified)

Guttenplan Consulting LLC

Advising & consulting services for innovative companies, both big and small, at the cross-section of financial services and technology.

✓	Delivered product-led growth (PLG) strategy, product roadmap, & product operations plan to a startup in the mortgage lending & investment space, allowing them to accelerate growth by entering a new market and launching new products.

✓	Led redesign of a mobile app (iOS / Android) and a digital credit application for a Credit Card / Payments startup, and delivered the strategy to get the company from beta to full launch.

✓	Advised data science team at a top technology player in the automotive industry, enabling them to build & refine advanced AI / machine learning (ML) models to accurately predict auto loan pricing for eCommerce customers.

✓	Helped Enterprise Software startup to launch and go to market with their SaaS product, assisting with the business development, product planning, & delivery of the product with their first two major clients.

✓	Educated and advised early-stage credit / lending startup team, resulting in a well-timed pivot from an undistinguished consumer product to an SMB product with massive opportunity in underserved markets.

✓	Worked with a Top 10 independent auto finance company to help rebuild a product management team, prioritize a product roadmap through deep user research, and redesign a B2B2C user experience.

Advisor & Consultant - Product | Strategy | Leadership | Risk | Data & Analytics

Simplist

Series B FirstMark-backed B2C marketplace and SaaS platform (still in stealth). First executive hire, brought in to build the Product Management & Product Design functions, and to enable rapid product expansion. Helped Simplist become America’s fastest-growing mortgage company, as it achieved the milestone of $1B in loans originated in early 2022 (within 24 months in operation).

 ▪ Led the launch of 14 new US states to expand to serve more than half of the US consumer population (from 6 states), helping the company to earn close to 8-figure revenue in 2021 (at Series A).
 ▪ Building the Product function, first as the sole PM supporting 20 engineers through the Series B fundraise, and now expanding to a high-performing team of 4 Product Managers & Product Designers and growing.
 ▪ Focused on providing the best user experience, as evidenced by our 4.98/5 average rating (based on ~450 reviews).
 ▪ Partnering with a top US mortgage lender to develop their first 3rd party originator API solution.

VP of Product

PeerStreet

Series C a16z backed marketplace platform revolutionizing real estate debt investing. Executive team member leading Product Management, Data Analytics, & Product Design (managing 15 FTE); Scrum Agile development. 

 ▪ Resuscitated a business severely damaged & halted by COVID and have grown it to $60M monthly volume (and accelerating) through combination of operations team enablement, innovative SaaS features and improved UX for lenders & brokers, and new features to eliminate end user friction (borrowers).
 ▪ Launched Pocket, a 2% yield investment product, to serve retail investors with idle cash on the platform, attract new cash & retail users to the platform, and provide low-cost warehouse funds for PS. 
    ➝ 1k+ users & $10M in first 60 days of beta launch; a valuable expansion to product portfolio.
 ▪ Increased tech productivity by >50% YoY by providing clear strategic direction, building prioritization & approval processes, launching PI Planning, hiring top talent, and actively coaching & mentoring my teams.
 ▪ Developed automated distribution & disbursement technology, increasing speed and transparency for investor payments (big UX wins), eliminating costly data errors, & creating SaaS architecture foundation.
 ▪ Coached & developed product teams, which grew from 9 to 15 full time PMs, Product Designers, & Analysts.

VP of Product Management

OnDeck

Hired to develop new company vision & product roadmap, launch new products & features, and scale the product and engineering orgs. Role grew to become interim Head of Product, overseeing department operations, budgeting, and managing 17 team members (directors, PMs, & UX designers) across product strategy, product development, & UX design teams

▪  Grew Product & Design Org by 40%, and in the process greatly increased diversity of the team; Promoted 7 individuals, all of whom improved the number of underrepresented voices at senior levels.
▪  Built and owned the roadmap for the full product lifecycle, and led the end-to-end product development process and go-to-market (GTM) execution across all business areas.
▪  Led strategy to drive Line of Credit product relevance, which involved delivering faster funding solutions, changing product structure, and restructuring sales incentives, resulting in the product becoming a significant contribution to profit (>20% of portfolio originations, ~40% increase YoY, and 10% utilization increase).
▪  Identified, delivered, and drove adoption for innovative Instant Funding feature that solved customer problem of not receiving funds fast enough on draws, resulted in feature adoption across 25% of entire LOC portfolio and ~$15M additional draw volume in first year of launch.
▪  Rebuilt the API-based bank data delivery and extraction process for customers, significantly improving UX and increasing client acquisition funnel conversion by eliminating need to provide bank statements.
▪  Overhauled and modernized Website front-end UX and back-end architecture & site analytics, improving top-of-funnel volume, SEO ranking, and conversion rate, as well as better understanding of user needs & behavior.
▪  Determined OnDeck’s next lending & non-lending products & features through deep user research, market research, and competitive analysis, gaining Board level approval to pursue new solutions to enable sustained growth & market relevance.

Vice President of Product Management

Capital One

Developed product roadmap for $50B consumer auto loan portfolio with over 3M prime and subprime borrowers. Led cross-functional Lean Agile team of 30, which included PMs, business analysts, software engineers, project managers, & data scientists. Product strategy included website, mobile apps (iOS / Android), email, mail, & live agent.

▪ Built Auto Finance’s first web & mobile experience for past due consumers, including a digital payment plan setup tool, reducing agent costs by eliminating unnecessary calls, as well as improving customer experience and helping digitally savvy consumers who didn’t want to speak to agents get current on their loans.
▪ Leveraged customer feedback, data science, and analytic methods to drive a key policy change, adding $5M profit per year to the company and helped consumers to avoid $5M in loan defaults per year.
▪ Built Capital One Auto Finance’s first digital communication strategy for delinquent borrowers, which greatly reduced losses and operating expenses, and kept many more customers driving their cars.
▪ Redeveloped the business strategy playbook for the next recession, better positioning Capital One to achieve financial goals through the next credit cycle.

Head of Product Strategy, Auto Finance Customer Servicing

Monitored & advised the Small Business banking division. Owned all business & risk metrics & analysis used to oversee and govern each product line (lending, corporate cards, deposits, treasury management services, merchant payments acceptance). Acted as Divisional Credit Officer, Credit Governance Advisor, and owned all Data Governance frameworks.

▪ 	Advised business executives on key strategic decisions and growth initiatives, enabling the national launch of Spark-branded small business products and the development of a new underwriting technology system.
▪ 	Re-engineered credit data and reporting infrastructure using innovative Tableau data-visualization tools and automation to give executives more robust, timely, and accurate information for critical decision making.
▪ 	Developed and owned all risk policies and risk governance framework, enabling the business to launch new strategies and grow in a well-managed way
▪ 	Completed proprietary ACC credit leadership training program (executive nomination required).

Director of Credit Strategy and Analysis, Small Business Banking Credit Risk Management

FTI Consulting

Provided expert consulting services for major financial services institutions, leveraging 10+ years of industry experience. Drove business development, led consulting teams, and managed client relationships & budget for projects supporting 2 of the top 4 US banks following the real estate crisis. Engagements focused on capital markets players involved with mortgage-backed security (MBS) structuring, underwriting, due diligence, and trading.

Senior Director, Financial and Enterprise Data Analytics

Wells Fargo Bank

Vice President, Consumer Risk Asset Review 2008-2011
Vice President, Home Equity / Consumer Credit Group 2005-2008
Data Science & Credit Risk Management, Business Banking Group 2001-2005

Vice President, Consumer Risk Asset Review
Oversaw all consumer & small business credit portfolios from shareholder perspective to ensure optimal business practices. Led examinations with focus on soundness in underwriting, account management, servicing and collections, mortgage foreclosure operations, debt restructuring, risk modeling, fraud mitigation, real estate & collateral valuation, risk-based pricing, loss forecasting, reserve levels, & business metrics / KPIs. Identified areas of significant risk and opportunity, and made recommendations to influence executive leadership.

▪	Uncovered risks in mortgage originations and servicing units that led to critical policy tightening during the early stages of the recession, resulting in tens of millions in loss reductions.
▪	Analyzed small business lending sub-portfolios through the credit cycle and forecasted return on assets to identify unprofitable segments, resulting in leadership exiting these segments to increase portfolio profitability.

Vice President

Fair Isaac, & Co.

Data Scientist
Worked on various stages of development for 4 separate FICO scores and the new MyFico.com site.

Analytics Engineer, Credit Bureau Risk Modeling Group

Product, Strategy, and Data Analytics leader turned consultant and executive coach.

Over 23 years experience working in consumer & financial services, data, SaaS, and technology industries with a versatile GM skillset and expertise across Product & Design, Credit & Risk, Data & Analytics, Finance & Strategy, and Operations. Proven track record of developing and bringing to market successful strategies, products, and processes across fintech innovators such as Simplist, PeerStreet, & OnDeck, as well as established players Capital One, Wells Fargo & FICO. I’m articulate, resourceful, dependable, and passionate about technology innovation. UC Berkeley Engineering & Berkeley Haas MBA.

As a Coach, I have helped 100s of people find their purpose, advance their careers, and confidently step into leadership roles. I am an ICF Member and draw from my training in Transformational, Ontological, Ecological Coaching, and Mindfulness, as well as my many years as an empathetic corporate leader. 

I coach:
👉️ Organizational leaders and managers
👉️ Entrepreneurs and business owners
👉️ High potential emerging leaders

Connect with me here: www.leadingyourlife.co
You can also learn more about my coaching journey here:

Apple: https://podcasts.apple.com/us/podcast/160-jeremy-guttenplan-on-transformation-relationships/id1143850229?i=1000678323011
Spotify: https://open.spotify.com/episode/5p50QAwwD6eQRD8Hkxc09i?si=3eHPqoEDQry6V6P8FlBIwg

A bit more:
I'm passionate about serving people, whether it's understanding the needs of my clients, training my students, or leading teams as a player-coach and mentor. I've grown and built several high-performing teams in fast-paced environments, ensuring my team members have everything they need to be focused and successful.

Most people work in perpetual motion.

Switching tabs.

But if your brain feels like a browser with 47 tabs open...

...And 46 of them are frozen?

That's what decision-making can feel like in senior leadership. 

Every choice feels massive. Every "what if" keeps you awake at 2am.

74% of leaders reported experiencing a ten-fold increase in daily decisions over the past three years...

...And 86% of them say this information overload makes decisions more complex. (Oracle, Decision Dilemma Global Study, 2023)

Here's the thing though...

The cure isn't in delaying or gathering more information. All the excess noise is where the real block is.

I learned this the hard way after spending three weeks deciding which coffee maker to buy. Three weeks. For a coffee maker.

While I was researching grind settings, my business decisions were piling up like dirty laundry.

That's when I created what I call the "Stop Being Weird About Decisions" framework.

Before any big choice, I ask myself three simple questions:

1. Does this align with what actually matters to me? (my values)

2. If I say yes, will this move me closer to, or farther from, my goals?

3. Can I move forward in a way I’d be proud of, even if the result isn’t perfect?

That's it.

No spreadsheets. No pros and cons lists that go on forever.

Most decisions that feel huge today won't matter in six months anyway.

The coffee maker I eventually bought? It broke after four months. But my business kept growing because I stopped getting paralyzed by small stuff.

The leaders I coach use this and tell me they finally feel clear enough to stop second-guessing and move forward with confidence.

If you're stuck on a decision right now, try out those three questions above.

Or if you want someone to talk through it with you, shoot me a message.

Jeremy Guttenplan, MBA, PCC

Business Coach | Executive Coach | Leadership Trainer | Business Advisor | Former Product & Tech Executive

Patterns you don’t face, you repeat.

I used to sabotage every relationship I'd ever been in.

Jobs, friendships, my marriage. If there was a way to mess it up, I'd find it.

A meta-analysis of 11 regret-ranking studies shows that people's biggest regrets are a reflection of where in life they see their largest opportunities.

(Source: Roese, N. J., & Summerville, A. (2005). What We Regret Most … and Why. Personality and Social Psychology Bulletin, 31(9), 1273–1285)

Then I became a father and something smacked me like a bucket of ice water to the face.

It wasn't just the whole "holy crap I'm responsible for a tiny human" thing. It was realizing that I was now my son's example of what a man looks like.

And I absolutely hated what I saw in the mirror.

I was operating in full victim mode. Blaming everyone else for my problems. Avoiding any real accountability like it was the plague.

On paper, I looked like I had my stuff together. Behind the scenes? I was a complete mess.

I'd sabotage jobs I was actually good at. Destroy friendships I desperately needed. Put my marriage at risk over stupid stuff.

The more I avoided looking inward, the more I repeated the same destructive patterns over and over.

Here's what I finally learned: patterns you don't face, you repeat.

No promotion or pay raise can fill an internal void. No new relationship can fix what's broken inside.

Until you confront the root cause, you'll keep playing the same crappy story in different places.

If you feel like you're silently failing even when everything looks good on the outside, you're not broken.

You're just carrying unhealed parts into your work and relationships.

The breakthrough isn't about achieving more stuff. It's about pausing long enough to ask yourself one simple question:

"What pattern am I repeating that I actually need to face?"

That question changed everything for me.

Two and a half decades of leadership taught me this: Trust rarely dies in big moments. 

It dies in the little ones we often ignore.

I lived with undiagnosed ADHD for most of my corporate life.

And while I was good at solving problems, I was also impatient.

I’d cut people off. Get frustrated too quickly. React before listening.

I didn’t mean to, but those small moments chipped away at trust.

Colleagues felt dismissed. Teams grew cautious.

Relationships I needed to build ended up strained.

Here’s what I’ve learned:

Your team’s trust won’t be built in grand gestures. It’s created (or destroyed) in small moments like these.

For over 40% of workers, poor communication reduces trust both in leadership and in their team. 

Remote workers are more affected, with 54% reporting poor communication impacts trust in leadership...

...and 52% reporting it impacts trust in the team. 
(Forbes, The State Of Workplace Communication, 2023)

Most leaders think communication is about getting your point across.

But it’s really about being responsible for how your words land with the people who matter most.

Here are five sentence frameworks that build trust instead of destroying it:

“What would it look like if this succeeded?”

“What I need from you is ___ so we can ___.”

“Here’s what’s working well... Here’s what will make it even better...”

“I can commit to ___, but I can’t commit to ___.”

“What’s one thing I can do to make this easier for you?”

When leaders use these, meetings end with alignment. Feedback builds motivation. Boundaries are respected.

What other phrases have you found that help build trust?

If personal habits showed up on a balance sheet, many leaders would be bankrupt by Q2.

Think about it like this - every habit you build is either making deposits or withdrawals from your future self's bank account. 

The sneaky part is that most leaders only look at the immediate transaction without checking the long-term statement.

Take morning routines as an example. The immediate ROI might seem terrible. 

Say you wake up 30 minutes earlier to exercise, meditate, or plan your day. 

That's 30 minutes you could have spent sleeping. The instant return feels negative.

But here's where it gets interesting. 

Six months later, that same leader is making clearer decisions, has more energy for important conversations, and isn't hitting the afternoon crash that used to derail their productivity. 

The compound interest on that small daily investment becomes massive.

The flip side is equally true but way more painful. 

A University of Scranton study found that 80% of big goals fail within six weeks. Not because people don’t care, but because the goals are too big to sustain. Micro-habits, by contrast, are proven to boost adherence and create steady gains over time.

Say you skip strategic thinking time because "there's too much urgent stuff to handle." 

The immediate ROI looks great - you tackled seven fires and felt productive. 

But the long-term cost is brutal. You're always reactive, never proactive, and your team starts making decisions without you because you're too busy being busy.

Most senior leaders are financial wizards with company budgets but completely broke when it comes to personal habit accounting. 

They'll analyze every line item on a quarterly report but never audit how their daily choices are performing.

The leaders who get this right do more than succeed. They create systems that work even when they're not working. 

That's what separates good leaders from unstoppable ones.

Let’s crowdsource: Which habit is your best long-term investment?

(Pic tangentially related: this fluff made a habit of trying to steal my food)

This sneaky bug in your brain's programming is keeping you stuck.

It's like running your life on autopilot with you in the cabin instead of the cockpit.

I used to be the king of playing it safe.

In corporate meetings, I'd nod along even when I disagreed. I'd prepare backup plans for my backup plans. 

Everyone thought I was "strategic."

Really? I was just scared of failing.

Here's the weird thing about our brains. They have this sneaky quirk. 

It's like your brain puts you in the passenger seat of your own life.

Your survival mode kicks in and suddenly you're avoiding everything uncomfortable. 

Hard conversations. New opportunities. Anything that might rock the boat.

Nearly 70% of HR leaders say burnout has increased in their organizations over the past year. 
(Unmind survey of 3,625 Leaders, 2024)

I get it. It feels safer to stick with what you know.

But here's what nobody tells you about "playing it safe."

Safety at all costs becomes a prison.

I spent YEARS in that prison. From the outside everything looked great. Good jobs. Nice titles. Steady paychecks.

Inside? I was slowly dying.

The stress kept building. My energy kept draining. 
My relationships suffered because I was always trying to keep everyone else happy.

Sound familiar?

That pattern of avoiding discomfort actually multiplies it. It's like trying to hold a beach ball underwater. 

Eventually it's gonna pop up and smack you in the face.

The hard truth is this: survival mode doesn't preserve your security. It preserves your stuckness.

Once I finally stepped out of that mode everything changed. 

Instead of fog I had clarity. Instead of panic I found peace. Instead of treading water I found real freedom.

And that's when actual growth begins.

I talk leaders through this all the time. Shoot me a message if you want to bounce some ideas.

Taplio

Jeremy Guttenplan, MBA, PCC's Linkedin Analytics

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