I help high-achievers thrive in work and relationships 💙 | Business strategies that work on humans too | Remote wisdom from 25+ countries

Why do we use our best frameworks at work and our worst habits at home?

What if the playbooks you use to save $100K+ accounts could also save your relationships and closest friendships? 

I learned this the hard way.

After 5+ years in CS, managing $10M+ ARR, I almost lost my most important account: myself. The same frameworks I used to keep customers loyal also saved my relationships and rebuilt my life:

- Resolve conflicts before they explode
- Communicate proactively so people feel seen
- Deliver value without burning out
- Build trust that lasts

They work in business, dating, friendship, with any human, in any context, and they’re something AI can’t replicate.

Now I share what actually works:
→ Business frameworks that improve work and relationships
→ Remote work wisdom from 25+ countries
→ GTM + CS strategies that scale humans, not just headcount

Because your 9-5 skills shouldn’t clock out at 5:01.

____

Hi, I’m Anthony 👋

CS leader, remote work advocate, and lifelong learner passionate about growth, habits, and helping people thrive without burning out.

Whether you're:
→ A leader looking to strengthen teams and client relationships
→ A remote professional balancing career and connection
→ Or a high-performer ready to apply proven frameworks outside of work

You're in the right place.
📬 Reach out to collaborate, connect, or just say hi!

I’m on a mission to build something bigger: a platform to help high-achievers escape burnout, embrace remote work, and design lives they don’t need to escape from.

____

As a CSM, I’ve: 

→ Scaled departments from $350K to $1.5M+
→ Managed $10M+ ARR across global SaaS accounts
→ Boosted LTV by 279% with better onboarding
→ Cut churn by 15% through scalable playbooks
→ Closed and led companies' biggest deals
→ Built AI-powered systems that scaled adoption + self-service
→ Mentored and coached new CSMs to performance faster

Behind every metric is the same philosophy: when you create people-first experiences with smart systems, growth runs on autopilot.

Anthony Boudreau

UpdateAI

ChatGPT my way to success. All day, every day.

Co-Founder, Head of GTM

SuccessHACKER

SuccessHacker is focused on bridging the gap between theory and execution. Offering consulting, talent management, industry training, and an open community for Customer Success professionals, teams, managers, and leaders. SuccessHacker teaches you how to do Success right, so you don't lose your most valuable resource, your customers.

Success Coach

GTMramp

Limited Partner

Zuora

Responsible for partnering with the success leadership team to identify areas of opportunity & inefficiency, provide recommendations to drive improvement in those areas, and champion consistently improving business performance.

Bring impact in this role through analytical problem-solving, leading a high-performing team, partnering with senior cross-functional leaders and engaging the SaaS customer journey alongside overall business growth.

Driven, curious, intelligent and deeply passionate about Customer Success. 

Key Objectives
• Own the Customer Success program, process, team enablement, data insights and tracking with the goal of improving the customer journey for our customers
• Implement and iterate on Zuora's Gainsight instance
• Own and lead CS playbook formation and activation across the Zuora product offerings, driven by CS data & insights (ie product analytics, automated customer outreach, consumption metrics, integrations, etc)
• Build & drive process, change management, systematic practice and tooling for Customer Success across product lines
• Guide key cross-functional relationships as the owner-in-team of customer engagement KPIs including renewal/churn indicators, growth & usage trends and CSM performance metrics
• Be a confident, hands-on organizational visionary with the ability to do the work, as well-- you can see what needs to be done and work backwards to drive execution based on data
• Coordinate with Customer Success and cross functional leaders and earn credibility through your expertise on process and systems as a strong communicator and effective influencer.
• Lead with creative problem solving, and leverage data to drive influence and strategy while thinking of systems holistically

Manager, Customer Success Strategy and Operations

Fivestars

Develop and implement lifecycle processes, policies, and metrics to support customer outcomes and business growth, assisting to define appropriate touch points (i.e., human-led and digital) throughout the customer journey (pre and post initial sale)

Identify opportunities for process automation and optimization, with a focus on scalability and driving significant growth.

Collaborate with Customer Success leadership to develop training and enablement to drive efficiency
Support the development and rollout of systems and digital tools to improve the team’s effectiveness and efficiency and provide increased customer insights through data, automation, and telemetry

KEY WINS
- Routinely presents findings and makes recommendations to C-Suite
- Performed 3 month Six Sigma analysis to identify 3 key drivers to cut future Support overhead by 50%
- Redesigned onboarding content, playbooks, and processes for a 6000 customer / yr core product
- Managed 12 remote CSM’s and increased their output productivity by 30% in 5 months
- Rearchitected a 7 year old Salesforce object, mapping the object to client outcomes, and decreasing average administrative work by 30 minutes per/rep/day
- Using Salesforce analysis, Identified a 6 year mis-reporting of key KPI for customer time-to-value during onboarding 
- Success in the key items above led to scaling our alpha launch from 1 to 1300 customers in 18 months while shrinking the team size by 25% via attrition without need to backfill representatives

Customer Experience Analyst and Program Manager

FiveStars is the rewards program for small businesses that’s proven to bring customers back more often. Through unique rewards and personalized service, FiveStars helps everybody be a VIP. Founded in 2011 and based in San Francisco, our mission is to help businesses and communities thrive by turning every transaction into a relationship. In 2017, FiveStars drove 80 million in-store visits across over 12,000 local businesses in the U.S. and Canada. Over 31 million consumers use FiveStars to have exceptional experiences with local businesses. To-date FiveStars has raised $105 million from top-tier investors including HarbourVest, Menlo Ventures, Lightspeed, DCM, and Y-Combinator.

In this role I rely heavily on relationship building, strategic thinking, analysis, and empathy to drive key performance indicators. My sole focus is the success of our merchants. Some ways I have showcased my abilities are:

-Designed one-to-many “Loyalty Report Card” engagement campaign to increase product adoption
-Manage all post-sale customer touch points for $1.5 million ARR book of business
-Identified bucketing opportunity for inbound requests to enable increase in 1:1 productivity by 60%
-Piloted self-onboarding program to reduce training resources and increase product adoption
-Implemented empathy-based feedback mechanisms for product engagement to drive Objectives and Key Results

Senior Customer Success Manager

FiveStars

As a Training Manager at FiveStars, I served a role as both a strategy and execution contributor. While reporting to the VP of Operations I was the sole Training Manager and responsible for 50 team members. As it is in any startup, my role encompassed many different competencies. I was responsible for being a subject matter expert, project manager, key stakeholder, instructional designer, change manager, and facilitator of learning. Here are some points about what made me effective in this role:

Launched training initiatives across 53 team members designed to improve core performance metrics
Support customer satisfaction increased by 15%
Strategized and executed on key onboarding objective to increase 60 day survival rate by 18%
Collaborated with VP-Level stakeholders on sales-pitch revamp designed to increase close rate by 20%
Established four levels to measuring learning - NPS, knowledge retention, behavioral changes, and business outcomes


Below were some of my core responsibilities:

-Analyze the needs of an organization to determine the necessity of training as a tool to close performance gaps 
-Layout project plan with milestone, deliverables, and responsibilities
-Design and develop content that is engaging, progressive, and leverages the principles of adult learning to maximize retention
-Implement effective training strategies to improve key performance indicators
-Evaluate the efficacy of training as it applies to all four levels of Kirkpatrick's Evaluation methods
(Net Promotion Score, Retention, Behavioral, and Business Outcomes)

I believe strongly in the power of intrinsic motivation and strive to understand my peers' motivation to learn.

Training Manager, Operations

As a Senior CRS I was responsible for many tasks related to retaining customers and managing a team of 4. Though my core function was customer facing, I was also involved in many strategic tasks. Here are a few items that I delivered on to enhance the department:

Utilized sales and solution based skills to increase retention of clients by 25%
Recreated process for inbound cancellation requests to increase rep capacity by 50% 
Created playbook for new team members that increased ramp up speed by 100%
Reduced churn by 18% through analysis of Salesforce cohorts and identification of early life cycle signals

Some info about what I did in the role:
Churn analysis, cohort analysis, process improvement, customer lifetime value calculations, renewal goals, and cross functional delivery of key takeaways. This allowed me to operate at a high degree and still deliver over $1.2 million in retained revenue. 

I deployed a variety of tactics and skills to achieve this:
-Empathy and Relationship nurturing
-Simple and Customer Rapport Building
-Consultative Selling 
-Objection Handling
-Statistical Analysis
-Pattern Identification
-Probing

These methods were effective in retaining 40% of clients totaling $1.2 million in customer lifetime value.

I took my learnings from this role to develop a more effective strategy of selling the FiveStars product. There is a large problem for America's small businesses that FiveStars, and myself, have uncovered. If you've read this far, reach out to me and I'd be happy to share more.

FiveStars is a loyalty program for small businesses in the US. Their mission is to help  businesses and communities thrive by turning transactions into relationships.

Senior Client Retention Specialist

Intuit's Demandforce

• Pioneered teach-back system to reinforce solution selling, objection handling, and closing skills
• Launched emerging market vertical to expand addressable customer base by 12%
• Developed need analysis card game to practice probing skills 
 
Some more info about the role:
Utilize solution sales and territory management to hit quarterly sales targets
Through lead generation and referral programs, build pipeline of qualified opportunities
Manage launch, on boarding, and training timeline

Account Executive

AT&T Mobility

•	Manage business accounts from 5-500 employees (Yammer, Eventbrite, Ubisoft, WRNS Studios, Osterhout Group, Oracle Racing, and others)
•	Proactively identify upsell or cross sell opportunities to increase account Annual Recurring Revenue
•	Provide first level supervision, escalations, and support for team members
•       Identified opportunity to increase upsell opportunities within business units through needs assessment, resulting in an increase of 25% ARR for Oracle Racing Team
•       Utilized retail connections and consultative selling skills to grow same store sales 145% year over year
•       Implemented role plays to increase adoption of new products by 50%

Retail Business Consultant

- Husband and Father (both are women. #GirlDad)
- I'm a fan of AI
- I disc golf
- I Lego
- I love movies like Ghostbusters (original), The Matrix, A League of Their Own, The Big Lebowski, Dogma, Shawshank Redemption, and About Time. To name a small fraction.


My Top 3 skills: 

1. Learning
2. Finding big problems
3. Knowing who can fix big problems (even if they don't yet know they can)

I love chatting with people. Shoot me a text at 415-999-9425 (but expect delays)

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The Battle

Anthony Boudreau

Mickey Powell

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