You've been carrying
this team for years.
It's time to move up.
A focused 2-hour working session to get clear on what you actually want next, reframe what your CSM experience is worth, and identify the exact role where your skills finally get the recognition — and the pay — they deserve.
Book Your Free Clarity CallNo commitment. No sales pressure. Just a conversation about what's next.
You're not burned out because
the work is hard.
You're burned out because it's invisible.
You manage relationships that generate millions in retention revenue. You train new hires. You de-escalate crises before they reach leadership. You onboard enterprise clients, build success plans, and carry the emotional weight of accounts nobody else wants to touch. And then you go home, look at your paycheck, and wonder how any of that adds up to this.
The problem isn't that you're not good at your job. You're excellent at it. The problem is that "good at your job" in Customer Success often means being so indispensable where you are that nobody — including you — can picture you anywhere else.
- You know you're ready for something more — but you can't quite name what that is
- You've been told you're "great with people" your whole career, and you're not sure if that's a strength or a trap
- You look at PM, AE, or leadership roles and think "I could do that" — but your resume doesn't say it
- You're staying in a job you've outgrown because leaving feels harder than staying
- You're not sure if you want a better CSM role, a completely different role, or something you haven't named yet
That last one is the most common — and the most important thing to figure out first. That's exactly what this session is built to do.
I've seen this
pattern dozens
of times.
I've coached professionals out of Customer Success roles and into PM positions, leadership, account executives, and entirely new directions they never saw coming. The skills that make a great CSM are wildly transferable. Most people just don't know how to say that yet — and that's the work we do together.
Three deliverables.
One session. Real clarity.
· Networking & Informational Interviewing
· Formal Job Interview Prep Checklist
· Working with Recruiters
· Salary Negotiation (with a job)
· Salary Negotiation (between jobs / multiple offers)
Plus homework assigned and a debrief call scheduled before you leave.
This is what the
session produces.
Below is Dylan's own Career Identity Narrative — built from 26 years of delivery at Charles Schwab, Oracle, LPL Financial, and the Texas Department of Agriculture. The document below is a PM narrative because that's Dylan's career. Yours will be built from your CSM experience and your specific next move — whether that's a better CS role, a PM title, a leadership position, or something you haven't named yet. Same structure. Your story. Built with someone who has been inside the companies and institutions you're trying to get into.
Built and practiced out loud in session. Use when someone asks "what do you do?" — networking events, interview openers, LinkedIn voice notes.
Use as the opening paragraph of your LinkedIn About section and as the basis for cover letters.
I'm a project manager and program leader with 26 years of delivery experience across financial services, technology, and government. I specialize in complex, multi-stakeholder programs in enterprise environments — particularly where there are aggressive timelines, high organizational visibility, and significant consequences for getting it wrong. My background spans both waterfall and agile delivery, and I'm equally comfortable leading structured program governance or running a scaled agile release train. I've worked at the program and portfolio level at Charles Schwab, LPL Financial, PNC Financial Services, and Oracle, and I currently serve as Agile Program Manager and Release Train Engineer at the Texas Department of Agriculture, leading a 40-person ART delivering systems that support over one billion meals annually.
Use as the framing for resume bullets, LinkedIn About section, and interview answers.
- Enterprise program delivery — Leading cross-functional, multi-vendor programs from initiation through go-live in high-stakes, regulated environments; managing scope, schedule, budget, and stakeholder alignment simultaneously
- Scaled agile execution — Operating as Release Train Engineer and Agile Program Manager in SAFe environments; coordinating work across multiple teams, managing PI planning, and aligning delivery to business objectives
- Executive stakeholder management — Translating complex technical work into clear business language for C-suite audiences; managing upward under pressure without losing the room
- Crisis recovery and risk mitigation — Parachuting into troubled programs, rapidly assessing root cause, and restoring confidence and forward momentum when delivery has stalled
- Cross-functional team leadership — Building alignment and accountability across teams that don't share a reporting structure; creating shared ownership in matrixed, distributed, multi-time-zone environments
- Delivery at scale — Leading programs that affect millions of end users, processing billions of transactions, and coordinating dozens of contributing teams simultaneously
Use as the basis for your LinkedIn About section and your answer to "tell me about yourself" in long-form interviews.
I came up as a working project manager — not someone who studied PM and then practiced it, but someone who got dropped into complex delivery situations early and had to figure out how to make them work. Over 26 years, those situations got progressively larger, more complex, and higher-stakes.
At Charles Schwab, I led the team that delivered the Trader's Dashboard for the TD Ameritrade–Schwab merger — a program that served 6 million clients and required coordinating delivery across one of the most watched integration projects in financial services history. I also coordinated the largest mobile app release in Schwab's history. These were not small-team, low-visibility efforts. They were programs where the right answer mattered, the timeline was non-negotiable, and the number of stakeholders with opinions was significant.
Before and alongside that work, I delivered programs at LPL Financial, PNC Financial Services, Dun & Bradstreet, and Oracle — across four continents, across waterfall and agile methodologies, and across industries with very different definitions of "on time" and "good enough." I've run programs with external vendors, managed consulting teams, and operated inside organizations where I was the person the president's office called when something needed to be fixed.
What I've learned is that delivery isn't primarily a technical problem. It's a relationship and communication problem. The organizations that deliver consistently are the ones where the right people are having the right conversations at the right time — and where the PM is making sure that happens. That's the work I've always done.
Use this to filter job descriptions and focus your application energy.
- Enterprise organizations (500+ employees) in financial services, technology, or regulated industries
- Programs with cross-functional complexity — multiple teams, vendors, or business units
- Organizations running or transitioning to scaled agile delivery (SAFe, LeSS, or equivalent)
- Situations requiring both delivery rigor and executive stakeholder management
- Senior Program Manager / Director of Program Management
- Release Train Engineer or Agile Program Manager
- VP / Head of PMO at a mid-to-large enterprise
- Strategic initiative lead in financial services or technology
- Single-team scrum master or delivery-only agile coach (underleveled)
- Greenfield startup without enterprise governance appetite
- Pure product roles without delivery ownership
Built from your actual experience and practiced out loud before you leave the session.
Your two or three go-to interview stories — pre-built, ready to deploy for any behavioral question.
| Story | Use When Asked About | Key Details |
|---|---|---|
| TD Ameritrade–Schwab / Trader's Dashboard | Complex program, high-stakes delivery, tight timeline | 6M clients, largest mobile release in Schwab history, merger timeline |
| President's office parachute assignment | Recovery, crisis, executive pressure, turning things around | Brought in to fix attrition-causing issues; turnaround credited publicly by direct manager |
| Texas Dept. of Agriculture ART | Recent experience, agile leadership, scale, mission-critical delivery | 40-person ART, 1B+ meals/year, government systems, RTE role |
Yours gets built the same way — from your CSM history, in a single focused session, with someone who has been inside the organizations you're trying to reach.
Book Your Free Fit CallFree clarity call first. No commitment. We'll make sure it's the right fit.
Two hours. Four blocks.
A direction you can act on.
This session is built for
a specific kind of CSM.
- ✓Have 3+ years in Customer Success, account management, or client services
- ✓Feel stuck, burned out, or like you've outgrown your current role
- ✓Know you want something different but aren't sure exactly what
- ✓Have looked at other roles (PM, AE, leadership) but feel unqualified on paper
- ✓Are ready to actually do something about it — not just think about it
- ✗Are brand new to CS and still finding your footing in the role
- ✗Already know exactly what role you want and just need tactical job search help
- ✗Are looking for someone to tell you what to do without your honest input
- ✗Aren't ready to be honest about what's actually not working
From burned-out CSM
to Project Manager.
Tania came in as a Customer Success Manager who knew something needed to change. She was good at her job — managing complex client relationships, coordinating internal teams, keeping accounts from churning — but she was exhausted and unclear on what she wanted next.
Through our work together, she got clear on the pattern: the parts of her CSM role she loved were actually project management. Coordinating cross-functional teams. Owning outcomes. Structuring ambiguous situations. She'd been doing PM work without the title — and without the pay.
Once she could see her own experience through that lens and talk about it with confidence, the path became obvious.
One session.
One price. No surprises.
- ✓Career Identity Narrative — written, all seven sections, delivered within 24 hours
- ✓Elevator pitch — built and practiced live until it sounds like you
- ✓Top 5 interview answers — written from your real experience, practiced in session
- ✓AI resume customization method — demonstrated live, repeatable for every application
- ✓Networking & Informational Interviewing Checklist and Script
- ✓Formal Job Interview Prep Checklist
- ✓Working with Recruiters: Screening Interviews
- ✓Salary Negotiation Playbook — When You Have a Job
- ✓Salary Negotiation Playbook — When You’re Between Jobs or Weighing Multiple Offers
- ✓Your next move defined — the role and direction worth pursuing
- ✓Homework assigned + debrief call scheduled before you leave
- ✓Session recording for reference
- ✓Starts with a free clarity call — no commitment required
We'll spend time on a call first to understand where you are and make sure this session is the right fit. If it is, we'll schedule your intensive. If it's not, I'll point you toward what is.
I've spent 26 years leading complex programs, managing stakeholder relationships, and watching smart, capable professionals get stuck in roles that don't reflect what they're actually worth. I've coached mid-career professionals through this exact transition — CSMs into Project Managers, Account Executives, Team Leads, and entirely new directions they didn't know were available to them.
The pattern I see most often: the person is excellent. The problem is how they're talking about themselves. That's the work we do in two hours — and the results tend to surprise people.
Still reading?
You already know it's time.
Let's figure out what's next.
The clarity call is free. The conversation is honest. The direction you leave with is yours.
Book Your Free Clarity Call