Hi, I’m Josh!

I build, fix, and scale Customer Success & Post-Sales.
Human led, AI assisted.

Over 15 years at critical inflection points across venture-backed, public, and PE environments, from $35M to $300M+ ARR, with an organizational psychology lens on retention, expansion, and outcomes.

Work With Me Connect with Me

Builder | Advisor | Transformation Leader

I bring clarity to chaos and structure to ambiguity by building scalable operating systems where discipline and accountability didn’t exist.

NorthSkye Advisory

NorthSkye Advisory is a selective executive practice for post-sales in B2B SaaS. I come in at inflection points to build, fix, and scale the operating model behind retention and expansion, and rebuild it for the AI era. The belief underneath it all is simple. Customer Success isn't a personality, it's an operating system, and AI should sharpen that system and give teams back time for customer outcomes, not replace the people who run it.

Explore How We Work Together

Perspectives in Practice

Most transformations don't fail because of the technology. They fail because nobody addressed the humanity of the change. I sat down with Nora Paxton on the latest episode of Executive Edge and dug into some of the unspoken challenges that are all too common. We touch on how leaders build trust and belief, using AI to amplify human capability, turning people from subjects of change into leaders of it, and addressing the fear underneath it all.

Change Is a Human Problem, with Josh Greenberg. Executive Edge with Nora Paxton.

Watch the Full Episode on YouTube Follow the Conversation on LinkedIn

Work With Me

Most organizations have the same revenue leaks. Onboarding that stalls, renewals that surprise you, and expansion that never compounds. I specialize in evaluating and rooting out those leaks to plug them, building the Post-Sales operating model that lifts net revenue retention and makes churn the exception, not the rule. That could mean standing up the motion, developing the leaders and teams who govern it, or taking full ownership of the outcomes.

Let's discuss the best option for you!

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1Tier 1

Operating Model Advisory & Build

Use Case

You're standing up post-sales for the first time, or you inherited a retention motion that's leaking revenue and needs a rebuild.

Capabilities

CS Operating Model DesignZero-to-One Function BuildsHealth Scoring & Risk FrameworksStrategic Planning FacilitationRetention & Churn RecoveryForecasting & Revenue VisibilityExpansion & CSQL PipelinesOnboarding, Adoption & Lifecycle DesignPlatform Selection & ImplementationAI-Assisted CS WorkflowsPost-Sales Operating RoadmapQBR & Executive Reporting Cadence

Engagement Models

Retained & Hourly AdvisoryProject BuildWorkshop Sprint

Outcomes

A post-sales motion you can forecast and defend, with renewal and expansion built into how the team runs day to day.

2Tier 2

Leadership & Team Development

Use Case

You're stepping into a bigger seat, managing a team for the first time, or your CSMs need to sharpen their strategic acumen to protect and grow revenue.

Capabilities

New-Manager CoachingCSM Pod CoachingSkills WorkshopsCSM Ramp & Enablement ProgramsCS Team Coaching & Enablement

Engagement Models

Monthly CoachingCohort ProgramHalf-Day Workshop

Outcomes

CSMs who lead the value, risk, and renewal conversations with confidence, and managers who coach instead of firefight.

3Tier 3

Fractional & Interim Leadership

Use Case

You've got a leadership gap or a transition, or you can't yet justify a full-time executive hire but need someone senior owning post-sales now.

Capabilities

Fractional CS & CX LeadershipInterim CS LeadershipStand-Up-From-Scratch LeadershipBoard & Exec-Team Representation

Engagement Models

Fractional (% FTE)Interim, Full-Time3 to 12 Months

Outcomes

Steady senior ownership of post-sales through a gap or transition, so the team holds together and the number stays owned.

How We Work Together

Step 1

Discovery Call

Step 2

Advisory & Build

Step 3

Team Development

Step 4

Fractional & Interim

Every engagement starts with a discovery call to check fit and scope the work. From there it deepens to match your situation, from a focused build, to strengthening the team, to holding the seat. Most start with a Post-Sales Operating Roadmap.

Ways to Get Started

Strategy Session

Spend one focused working session on a key problem you're facing, whether it's declining retention, building or restructuring a team, or a stalled growth motion that won't compound. Leave with a clear read and a directional action plan. This is the quickest way to gain clarity before committing to a broader engagement.

Book a Strategy Session

Post-Sales Operating Roadmap

Over the course of 2 to 3 weeks, I sit with your leadership and field teams, review your processes, tooling, and metrics, and give you an honest account of where the operating model stands. You get a written roadmap with the findings, the key priorities, the target operating model, and a sequenced plan, based on a timeline that makes sense for your organization.

Book a Discovery Call

1:1 Coaching

Not every effort is a full engagement. I coach Customer Success and Post-Sales professionals one-on-one, whether you're investing in your own growth toward the next role or for company-sponsored development. We sharpen the strategic instincts that protect and grow revenue, from the value and renewal conversations to the presence that moves you from a strong operator to a trusted leader.

Offered weekly or monthly, with a limited number of seats.

Book a Consultation

Don't see what you're looking for? Let's connect and discuss a custom option for you.

Fractional Customer Success & Customer Experience Leader, NorthSkye Advisory

Let's Talk

Operational Builds

I don't just write about theoretical abstracts. I build and operationalize them.

Flagship Builds

AI-Native Platform

Lighthouse Intelligence

An AI-native customer intelligence platform that unifies account signals, forecasts trajectory, and recommends the next best action for CS teams. Built to work with imperfect data and show its confidence rather than hide it. My distillation of over 15 years of operating judgment into a working product, with new capabilities shipping regularly.

Internal Tool

AI-Assisted CSM Prep Assistant

A working session companion that turns account telemetry, notes, and signals into a ten-minute prep brief before every customer call.

Operating Frameworks & Artifacts I've Shipped

Customer Success is an operating system. These are the repeatable frameworks I've designed and run.

Operating Model

At-Risk Account Governance Program

A structured program for catching at-risk accounts early, triaging them through clear entry criteria and executive review cadences, and recovering them with disciplined exit gates. Turned churn response from a reactive scramble into a repeatable operating motion.

Predictive Health

Health-Scoring Operating Model

Replaced gut-feel account health with a quantifiable, signal-driven model that combines product usage, engagement, support stability, and sentiment into a single trajectory view, so risk and expansion surface early enough to act on.

System

Risk-Signal to Playbook System

A library of targeted intervention playbooks mapped to specific risk signals, so the right play is prescribed the moment an account shows a particular pattern. Made CS intervention systematic and coachable rather than dependent on individual instinct.

Lifecycle

Customer Journey and Lifecycle Architecture

An end-to-end lifecycle model spanning activation through renewal and expansion, with stage-level objectives, leading indicators, and exit criteria that aligned Marketing, Sales, and CX around a single definition of customer progress.

Program

Voice of Customer and Advocacy Engine

Programs that turned satisfied customers into measurable advocacy, NPS, references, and public reviews, wired directly into the renewal and expansion motion rather than run as a side activity.

Analytics

Forecasting and Revenue Visibility

Built renewal and revenue forecasting tools from scratch and stood up reporting across multiple BI platforms, giving CS and leadership repeatable, scalable visibility into account health and trajectory, built with intention rather than guesswork.

Revenue

CSQL Pipeline Engine

Designed Customer Success Qualified Lead processes that turn frontline account insight into a structured expansion-pipeline source, run consistently across multiple companies to feed the growth motion.

Governance

Escalation and Incident Response Governance

Established global escalation and incident-response governance, severity definitions, customer communication standards, and executive update workflows that bring order and trust to high-stakes moments across Support, Engineering, and CS.

Sponsorship

Executive Sponsorship Program

Built an executive sponsorship program for strategic accounts, pairing customer leaders with internal executives to deepen relationships, surface risk early, and anchor long-term value.

Cadence

Renewal-Readiness Operating Cadence

A 180-day rhythm that surfaces renewal risk and expansion lift early enough to actually do something about it.

Scaled CS

Digital Engagement and Scaled-Touch Motion

A pooled-CSM and in-product nudge model for the long tail, so high-touch teams stay focused on accounts that move the number.

Org Build

Zero-to-One CS Function Build

Stood up an enterprise-ready Customer Success organization where none existed, from operating model and tooling to playbooks, scorecards, and team, across a multi-region, multi-segment book.

Shipping Weekly

More in Progress

I build something new most weeks, new tools, frameworks, and use-cases for the post-sales operating layer. Check back, or let's talk about what I'm working on now.

More Frameworks I've Shipped

CS Platform ImplementationCS Enablement ProgramsGlobal Knowledge BaseSales-to-CS TransitionCoverage and Capacity ModelingOnboarding and 30/60/90 FrameworksCoaching and Development ProgramsDigitized CS NewsletterProduct Feedback 360sRACI and Operating AccountabilityService Package DesignSOW and RFP ScopingExecutive Risk Reviews

In Their Words

“Josh built out standardized success methodologies, scalable onboarding frameworks, and data-driven health models that elevated both customer outcomes and internal performance. Josh is the kind of leader who turns complexity into clarity and vision into execution — a true force in modern, AI-enabled Customer Success.”

SVP, Customer Experience

“Working alongside Josh was a masterclass in modern Customer Success leadership. At Aprimo, Josh was instrumental in elevating post-sales and adoption strategy globally. He connected Product, Sales, and Services into a single rhythm, using AI-assisted insights and predictive health models...”

VP, Services & AI Operations

“A true beacon of adoption, operating at the highest of levels, bringing credibility to our AI story. If I were setting up my own business with a global team, I'd hire Josh in an instant! If Josh asked me to establish / help him set up a service provision in Europe, I'd willingly pause my retirement and help him achieve his objectives, such is the value of the guy.”

Regional VP, Customer Success

“When AI first emerged as a major force in our industry, Josh immediately recognized its potential. His ability to quickly grasp the technology, rally the team, and lead adoption efforts was remarkable. He brought real credibility to our AI story and guided us through change with clarity, confidence, and purpose.”

Enterprise Customer Success Director

“Josh helped drive standardisation across a global team of CSMs and built out processes that helped give clarity and clear direction... I'd recommend Josh to any organisation looking for an experienced and talented customer success leader who is capable of building a CS org that can scale while embracing AI solutions along the way.”

Sr. Director, AI Product Enablement

“He forms structure out of chaos in terms of the team's playbooks and internal processes for the CS team. Working in a global workforce inherently has its challenges, from unique requests to mismatched expectations, but Josh is able to collaboratively create a proper foundation and help define rules of engagement to ensure everyone is successful.”

Lead Customer Success Manager

“I got to witness Josh develop and roll out AI-driven programs and standardized methodologies that enhanced our operations... Josh created a fun, high-energy culture where everyone felt empowered to take ownership of their work and grow.”

Enterprise Customer Success Manager

“Josh has the ability to think both strategically and tactically, and leads by example. His support, vision, and drive helped contribute to many improvements at Sendbird. Just one of his many successes include building an engaging team culture that also elevated each individual (as well as the Customer Success organization.)”

AI Success Manager

SVP, Customer Experience

VP, Services & AI Operations

Regional VP, Customer Success

Enterprise Customer Success Director

Sr. Director, AI Product Enablement

Lead Customer Success Manager

Enterprise Customer Success Manager

AI Success Manager

Free Tools

Back-of-the-envelope models for the economics of running Customer Success as an operating system.

Assumptions

Shared inputs

ARR under management$10M

Fully loaded hourly cost100USD

Used across all three calculators.

Interactive

AI Capacity Calculator

A back-of-the-envelope look at the operating capacity returned when AI is layered into a CS team's weekly cadence.

Estimate

CSMs in scope10people

Hours saved per CSM per week8hrs

Hours returned per year

3,840

Capacity unlocked

2.0 FTE

Implied annual value

$384,000

Interactive

Operating Leverage Calculator

A back-of-the-envelope look at the operational value an operating system creates, the revenue it protects by surfacing risk earlier and the overhead it removes by replacing firefighting with governed cadence.

Estimate

Revenue at Risk

Baseline gross churn rate12%

Churn reduction from earlier risk detection20%

Operational Overhead

Hours lost to firefighting per week30hrs/wk

Overhead reduction from governance30%

Revenue protected per year

$240,000

12% → 9.6% effective churn

Overhead hours reclaimed per year

432 hrs

Overhead value per year

$43,200

Total operating leverage per year

$283,200

Interactive

Expansion Engine Calculator

A back-of-the-envelope look at the expansion revenue a CSQL motion drives when Customer Success systematically surfaces and converts growth in the existing base.

Estimate

Share of book with expansion headroom30%

Expansion capture rate from a CSQL motion15%

Expansion revenue per year

$450,000

Expansion NRR contribution

+4.5 pts

Three-year expansion

$1,350,000

Summary

Total Economic Impact

Estimate

Total annual economic impact

$1,117,200

Efficiency

$384,000

reclaimed capacity

Defense

$283,200

protected revenue + overhead

Offense

$450,000

expansion

On a $10M book, running Customer Success as an operating system is worth about $1.1M a year, $384K in reclaimed capacity, $283K in protected revenue and reduced overhead, and $450K in expansion.

About $3,351,600 over three years

Writing & Insights

Thinking out loud about leadership, AI, operating discipline, building things, and the human side of work.

AI Macro

AI Isn't Coming for Your Job. It's Coming for Your Job's Structure.

Why the disruption shows up in cost models before it shows up in headcount.

Behavioral CS Leadership

Customers Don't Churn over Features.

What a psychology background taught me about why accounts actually leave.

Cost Transparency

Opacity Is a Business Model.

Why you can't comparison shop for the things that cost you the most, and what happens when someone builds the tool that lets you.

Behavioral CS Leadership

Tolerance for Change Is the Real Ceiling.

I didn't have the resources is the respectable way to give up. The real ceiling on most teams is how much change they can absorb, not what they were given.

Builder Playbook

Zero to One Inside a Company That Doesn't Want a New Function Yet.

How to stand up something that didn't exist without permission you don't have.

Behavioral CS Leadership

Customer Success Needs a Seat at the Table.

The AI gap in CS is an investment problem, not a competence one. We've been handed a folding chair at a full table for too long.

AI Macro

The Displacement Nobody Is Pricing In.

Entry-level work, new graduates, and the broken first rung of the career ladder.

Behavioral CS Leadership

Every Churn Starts With a Warning Signal.

Retention has a check-engine light. The signals show up early. The discipline is building the system that reads them before the breakdown.

Personal

What a Hospice Social Worker Taught Me about Showing Up.

Lessons in presence from the person I'm married to.

Behavioral CS Leadership

Curiosity Is the Underrated Superpower.

Be curious, not judgmental. The leaders who ask the better question keep outrunning the ones racing to the better answer.

Cost Transparency

The Hidden Unemployment Signal.

The headline rate says one thing. The people who've exhausted their benefits say another. The gap is where the real story about AI and labor lives.

Behavioral CS Leadership

Crisis Management Starts Before the Storm.

The work that decides how a crisis goes happens before it arrives. By the time the storm hits, you're living off the preparation you already did.

AI Macro

When AI Goes Dark.

The day the models went down was a reminder. A single point of failure is still a single point of failure. Keep more than one arrow in the quiver.

Behavioral CS Leadership

The Retention Insurance Policy.

Nobody values the policy until they need it. The same is true of the proactive work that keeps an account healthy long before the renewal is on the line.

Builder Playbook

Build, Buy, or Own the Outcome.

The pendulum's swinging back toward building. When platforms pivot to owning outcomes and teams stand up their own customer systems, the buy-versus-build math changes.

Behavioral CS Leadership

From Good to Great.

Curiosity is the multiplier. The gap between a good leader and a great one is often just the willingness to keep asking instead of assuming.

AI Macro

Too Big to F(ai)l.

When AI labs start filing to go public, the bill comes due. I watched a company go public once, and net revenue retention doesn't hide on the open market.

Career Reinvention

Senior, Experienced, and Starting Over.

The quiet reality of leading at a high level while the market shifts under everyone.

The Throughline

Customer Success isn't a personality, it's an operating system that turns healthy relationships into a growth engine. I've held plenty of roles over the years, but the underlying mandate has never changed. Step into something undefined or underperforming, establish structure inside the ambiguity, and make it perform at scale. I lead with a discipline shaped by organizational psychology, treating retention and growth with a systems focus to ensure teams have the proper processes and tooling in place to deliver exceptional outcomes.

Where the operating instinct and the human lens both started.
- BA in Industrial and Organizational Psychology, the foundation for how I read teams, trust, and behavior change
- Early commercial and sales operations leadership, learning how revenue, accounts, and the day to day of a business actually run
Enterprise technology roles inside two of the largest US banks.
The discipline of release governance, clean deployment, and enterprise-scale migration.
- At Bank of America, owned release governance and end-to-end workflows for the Payments and Commerce portfolio, coordinating consecutive clean releases across platforms including BankAmeriDeals and the product that became Zelle
- At Truist, formerly BB&T, led enterprise application rationalization and data consolidation for a major migration, standardizing deployment and driving vendor cost savings
A FinOps and Technology Business Management platform that raised $136M in venture capital, with Andreessen Horowitz making its first-ever investment, before its 2016 Nasdaq IPO. Taken private by Vista Equity Partners in 2019 for $1.9B, then acquired by IBM for $4.6B. I joined at Series D and grew with the company through every stage of that journey.
Nearly eight years across progressive leadership roles in Professional Services and Customer Success, promoted post-IPO through the Vista Equity transition, scaling value delivery and maturing success motions across a complex enterprise customer base.
- Scaled the post-sales operating model across Professional Services and Customer Success, linking onboarding, adoption, and value realization to executive business objectives and renewal strategy
- Established health, risk, and escalation frameworks that stabilized enterprise renewals and improved forecast discipline in high-pressure cycles
- Built executive QBR and EBR narratives that translated cost, utilization, and value into the language of the C-suite, supporting multiyear commitments
- Shaped pricing, service packaging, and roadmap priorities as a senior voice in commercial and product decisions
- Standardized customer journey governance, improving renewal forecasting and expansion pipeline quality
- Acted as a senior escalation point and a bridge between Product, Sales, Engineering, Finance, and the C-suite, channeling Voice of Customer into roadmap priorities
A technology consultancy and managed services provider of TBM solutions, acquired by Accenture in 2022.
Consulting work shaping post-sales strategy, service offerings, and customer value for enterprise TBM.
- Defined Customer Success and post-sales strategy and service offerings for Technology Business Management solutions
- Partnered with Sales on RFPs, proposals, and statements of work for C-suite buyers
- Advised enterprise customers on TBM best practices, value realization, and ongoing Customer Success models
A Y Combinator company that raised more than $220M from investors including ICONIQ Growth, Tiger Global, and SoftBank Vision Fund 2. I joined at Series C when the company was valued at $1.05B, making it a unicorn in in-app messaging, voice, and video.
Built and led a multi-region Customer Success organization across more than forty countries and every segment, from digital and self-serve to strategic enterprise, for a platform supporting billions of conversations and hundreds of millions of users.
- Introduced predictive health scoring and renewal forecasting with early-action save plays
- Implemented Gainsight with success plans, scorecards, and a Value Maturity Framework focused on leading indicators and outcomes
- Revamped NPS, Voice of Customer, and G2 advocacy, and launched a scalable digital Customer Success model for long-tail customers
- Partnered with Product, Engineering, and Support on usage-signal gaps, incident response, and critical escalations
- Strengthened team culture and career pathing, developing individual contributors into team leads and building durable operating discipline
An AI-powered enterprise DAM and Content Operations platform used by global brands, owned by private equity firm Marlin Equity Partners and recognized by Gartner as a 2025 Leader, with additional recognition from Forrester and IDC.
Led a global Customer Success organization across AMER, EMEA, and APAC, spanning digital, mid-market, and enterprise, and owned the end-to-end post-sales journey along with CS budget, headcount and capacity planning, org design, and CX performance reporting for the private equity board.
- Rebuilt the global Customer Success organization across enterprise, mid-market, and digital segments, launching a new digital motion
- Built AI-assisted Customer Success workflows and targeted digital automations that increased CSM focus time and execution quality
- Redesigned health scoring and executive risk reviews to surface earlier signal and strengthen renewal strategy
- Standardized adoption roadmaps, success plans, and executive business reviews around outcomes and value realization
- Aligned Sales, Customer Success, Support, Services, RevOps, and Product around a governed post-sales rhythm and shared KPIs spanning GRR, NRR, and time to value
- Elevated market presence through customer advocacy, references, G2 momentum, and category leadership recognition
07
NorthSkye Advisory
An earlier career in sales, then over 15 years in post-sales across professional services and customer success, spanning financial services, Technology Business Management (TBM), FinOps, Communications Platform as a Service (CPaaS), and Marketing Technology (MarTech), and every environment from on-prem to SaaS to AI-native.

Worked With

A selection of organizations I've worked across over the last 15+ years.

Education

Master of Business Administration
IT Management & Project Management
University of North Carolina at Charlotte
Bachelor of Arts
Industrial & Organizational Psychology
Minors in Accounting & Finance
University of North Carolina at Charlotte
Activities & Leadership: Alpha Kappa Psi (VP of Finance), Dean's Fellows Program (Chair), Student Government Association, Alumni Advisory Council

Certifications & Training

Certified Customer Success Manager
SuccessCOACHING
AWS Certified Cloud Practitioner
Amazon Web Services
Certified Technology Business Management Executive
TBM Council
Six Sigma Green Belt Training
Bank of America

Recognition

Apptio Superstar Award, executive recognition for a Fortune 150 financial services program
Gainsight Visionary Award for data-driven customer experience improvements
Multiple-time Core Value Champion, consistently above the global leadership engagement benchmark
G2 Category Leader recognition, DAM at Aprimo and CPaaS at Sendbird

Core Competencies

Customer Success & Post-Sales LeadershipOnboarding & ImplementationAI-Assisted Operating ModelsNRR / GRR & ExpansionPost-Sales Strategy & OperationsHealth Scoring & Escalation ManagementTime-to-Value & ActivationDigital CS & Scaled MotionsExecutive Advisory & Cross-Functional AlignmentQBR & KPI GovernanceVoC, ROI & Value StorytellingEnablement & Coaching

Methodologies & Frameworks

MEDDPICCChallengerValueSellingSolution SellingDEARCustomer Lifecycle MappingAgileWaterfallPMBOKLean Six SigmaOKRsBalanced ScorecardRACITBMFinOps

AI and Automation