Clair Sullivan & Associates

Make Your Tech Career Layoff-Proof as a Solopreneur

Clair Sullivan

Founder and CEO of Clair Sullivan & Associates (a solopreneur business!)

Compare freelancing, consulting, and fractional work to identify which path fits your skills and goals.

Choose your solopreneur model

Bust the common myths that lead to the fear that keeps people from getting started.

Explore the fear that keeps people from getting started

Use a quick framework to test if solopreneurship matches your financial needs and risk tolerance.

Evaluate your business idea

Design Thinking is a creative approach to finding clarity amidst ambiguity. In this course, you'll be guided through how to apply Design Thinking to your own career exploration. The course itself is broken down into four sessions: Ground, Diverge, Converge, and Plan which will help you articulate your values, explore the career possibilities available to you, design experiments to figure out what you want, and plan your short, medium, and long-term next steps. You'll walk away with more confidence about what you want next and a roadmap for how to get there.

Clarify what you want with the help of Design Thinking

Course syllabus

Our course starts by grounding in where you are. Through a series of exercises, you'll reflect on your values, career experiences, and visions for your future. By the end, you'll be able to articulate what matters to you in your next step. *All live sessions will be recorded.

Module 1: Ground

This session is all about going wide. You'll canvas out three potential paths for yourself, quiet your inner critic, and ask what would have to be true in order to pursue each. By the end, you'll have three distinct paths and a research plan.

Module 2: Diverge

This session is all about making decisions. You'll synthesize what you've learned from your research and address some of your fears in making changes in your life. By the end, you'll clarify the direction you want to keep exploring.

Module 3: Converge

Here's where the rubber meets the road. You'll make an action plan with short, medium, and long-term goals, and design methods of accountability. We'll talk about addressing the inevitable barriers along the way, and you'll leave with clarity and conviction for what's next.

Module 4: Plan

Almost all coursework will take place during the live sessions, but there will be optional resources to continue exploring outside of class. *There will also be the (optional) opportunity to meet 1:1 with Simone

Weekly projects

Course schedule

Curious explorers who are ready for a change in their life but aren't clear on exactly what they're looking for

Overworked professionals who move a mile-a-minute but don't have the space to take a step back and reflect

Passionate generalists who feel pulled in multiple directions but aren't sure which path they want to choose

Who is this course for

Key outcomes

The North Star of this course is for you to go from messiness to clarity. We'll explore different frameworks for clarifying your personal values and career possibilities. You will walk away with conviction for what you really want from the next step in your work and life

A clear vision for the next step in your work/life

This course is actionable. From day one you will be envisioning, prototyping, and refining your path. You will leave with an air-tight action plan for the steps to take to keep progressing and resources that you can return to throughout your career.

An action plan with the short, medium, and long-term steps to achieve your vision

Accountability is everything. In this course you will connect with other folks who are in similar places on the journey. The relationships you form will extend long beyond the last day of class.

A vibrant community of other ambitious professionals to hold you accountable

In the course, you will receive a workbook filled with evergreen exercises, reflection prompts, and resources that you can dust off whenever you find yourself at a similar crossroads.

A buffet of research, exercises, and resources that you can return to again and again

Instead of spinning your wheels, follow a step-by-step process to determine what you value and plan your next move.

Simone Stolzoff

Cohort 9

Cohort 10

Don't wake up wondering what to do every day. Know that you've got an engine of job search working for you. The problem:Tech hiring has changed dramatically. Mass layoffs, shrinking headcounts, and decreasing venture capital has changed the math. There are more candidates than ever competing for a small number of roles. The competition is intense. The solution:Since 2019, our strategies have helped tech professionals secure over $400,000,000 in job offers. These clear, actionable systems get people more interviews, help candidates pass those interviews with flying colors, and land people top-of-market offers, even in this rough market. 80% of our clients choose between multiple offers. Your instructor:Sherveen Mashayekhi, Founder &amp; CEO of Free Agency• Backed by Maveron, Resolute, Bloomberg Beta, &amp; more• Product leader and technologist with a decade in hiring tech• Advisor and coach to tech executives across NYC and SF Proven results:• Hundreds of placements every year in product, engineering, design, marketing, and more• $400M+ in total offers since 2019, with &gt;80% of clients picking between multiple offers• $15.35M raised from industry-leading investors, executives, and 30+ of our own clients Frustrated by low response rates? Learn how to triple replies and uncover opportunities before anyone else. No gimmicks and no referrals necessary. Struggling to tell your story? Master storytelling about your career at a fundamental level, preparing you for any question or context. Worried about the competition? Implement frameworks to do better research, understand employers, and intentionally stand out at every stage. Course content: Day 1: Lay the foundations (docs + systems)﻿• Templates for resumes, cover letters, cold emails, LinkedIn, + so much more• Systems and tools to use to make the job search painless and efficient• Behind-the-scenes of ATS, LinkedIn Recruiter, &amp; other employer systems Day 2: Flood your calendar with interviews﻿• Advanced job finding techniques, including Boolean &amp; semantic search﻿• Actionable steps to take after submitting an app to 3x your response rate﻿• Strategies and templates to get to know someone at any company (but for real) Day 3: Win over recruiters &amp; hiring managers﻿• Masterclass: Personal pitch and career storytelling (prev. client: "game-changing!")﻿• Repeatable methods for identifying and leveraging recruiter and HM incentives﻿• Win outside the room: templates and nuances for pre- and post-interview comms Day 4: Beat the competition in the interview cycle﻿• Advanced coaching to become stellar at panel rounds, exec chats, case studies, interview homework, etc.﻿• First-of-its-kind framework for interview debriefs + analysis, enabling in-cycle adjustments and "hero stories"﻿• Deep dives on behavioral questions, leadership, end-of-interview moments - be the unforgettable candidate Day 5: Negotiate like a pro and secure the role﻿• Framework: how to seal the deal - to be the #1 pick instead of #2 - and take discrete actions toward winning the job • Behind-the-scenes of compensation systems, databases, and formulas used by companies to calculate offers﻿• Systems and templates for understanding, evaluating, and negotiating an offer (incl. scripts) Plus...﻿• What's the deal with 'hidden jobs,' ATS keyword matching, referrals... get the truth!﻿• Methods of analogy and loop-storytelling, incl. ways to enhance recall + fit through thank you notes, emails, and phone calls • Analysis of all stakeholders and incentives inside an interview process • &amp; so much more Job search has fundamentally shifted. In 2021, a senior PM or an engineering VP was so scarce and hot in the market that it took just weeks for them to find a compelling job with a top-of-market salary. In 2025, a senior PM job receives hundreds of qualified applicants, and dozens who are specifically qualified within the particular sub-industry of the company in question. And so you&nbsp;need&nbsp;to stand out. You need to look different on LinkedIn and in an email inbox. You need to tell your story in a way that goes beyond the "academic right answer," and instead differentiates you from your next peer over. Because how else is a hiring panel supposed to decide to pick you instead of that next person? And where do former clients now work?Companies like Snapdocs, Airbnb, Mozilla, Spotify, Fastly, TikTok, theScore, Zoox, Zola, Cruise, HBO, Kajabi, Lyft, Meta, mParticle, GitHub, Roblox, Peloton, Verizon, Tesla, Notion, Asana, Drift, Instacraft, Reddit, Yelp, Google, American Express, Clover Health, Upwork, Sonder, Oura, Pepsi, Dropbox, SoFi, the NYT, Amazon, Square, Check, Addepar, Electronic Arts, Disney, MLB, Angi, Shortcut, Coinbase, Lob, Roku, Rho, Cash App, Zoom, Motion, Matterport, Twitch, Gong, Chargebee, Wonderschool, The Athletic, January, Newfront, DraftKings, Expedia, Zillow, Shopify, just to name a few.&nbsp;Seriously, this is just a quick few. We're everywhere.

Redesign your job search process and interview strategy to compete and win.

If you can't make it, you will receive a recording of any particular session after it happens.

Every weekday for a week.

Do the homework during the course schedule and you'll receive specific and in-depth feedback. Take it with you afterward to use for future practice and refinement.

Async projects.

Ambitious individual contributors, managers and directors, and VPs already in tech. Minimum 3+ years of experience.

We're technologists who understand the nuances of product management, engineering, design, marketing, operations, &amp; everything in between.

You're actively job searching in tech or are planning a move in the next 6 months.

What you’ll get out of this course

You'll get systems and structures for every step of the job search process, built by people who know how hiring really happens, enabling you to take intentional actions at every step.

An entire job search engine, from your resume to your final offer

You'll see what an Applicant Tracking System (ATS) actually looks like, how recruiters use it, what LinkedIn Recruiter looks like, a live preview of a compensation database, alongside all the insights + nuances of how these systems are used (for + against) you. Get the intel!

Behind-the-scenes previews of what it all looks and feels like for employers

You don't have to start from scratch. Our templates, frameworks, and worksheets are proven in the tech job market. Start from strength!

Templates, frameworks, worksheets for your entire job search journey

We'll take your interview skills to the top 1%. Past students have put it best: "The interview and storytelling coaching was unbelievable. I'm going to be a better storyteller and negotiator for the rest of my life."

Advanced coaching to make you a STELLAR storyteller and interviewee

And even in 2024 and 2025, there's room to ensure you win not just a great job, but one that pays you well. Our negotiation framework will ensure you're politely but firmly capable of moving up any given offer, set up a competitive offer scenario, and avoid settling.

Data and frameworks to ensure you win & negotiate a top-of-market offer

Take control of your job search. Implement a proven system to get you interviews, win you the next round, and land you a high-paying offer.

Sherveen Mashayekhi

Founder & CEO @ Free Agency; fmr. Product Leader @ Stella (AI job matching), Toptal (jobs marketplace), founder @ JobHero (job search tools)

Learn how to confidently launch and grow a fulfilling independent consulting, advisory, or fractional practice.

Fractional VP, Startup Advisor, Founder

Rent the Runway

Modern Animal

Emerson Collective

Emily Hollender

Fractional Marketing VP | Startup Advisor | Founder of Next Wave Marketing

Cohort 2

Cohort 3

Is the thought of going out on your own both exhilarating and terrifying? I’ve been exactly where you are.You’re a seasoned operator. You’ve built teams, led complex projects, and climbed the corporate ladder. But turning that experience into a business of your own? That's uncharted territory.If you’re like most new fractionals, you’ve probably been spinning your wheels: tinkering with your website, sending cold emails with no replies, second-guessing your pricing, or wondering if you’re “doing it right.” The questions feel endless:→ How do I turn my expertise into an offer people actually want?→ How do I find and land my first clients?→ How (and what) do I charge?→ How do I set up the back-office of my business?I’ve been there. And after 3+ years, 30+ clients, and nearly doubling my 9-5 salary through fractional, consulting, and advisory work, I designed this course to give you the exact playbooks, tools, and guidance I wish I had when I started.Whether you’re ready to go all-in on fractional work, easing your way into it, or just looking to diversify your income outside of your 9-5, I'm here to help you kickstart your journey with confidence. I hope you'll learn with me!

It’s time to get off the sidelines and launch your fractional practice.

Articulate your positioning and offer suite that reflects your strengths

Tactical networking & sales strategies to build your pipeline

Proven techniques to scope, price & set up client engagements for success

Templates, tools, systems, and a clear action plan to go from 0 to 1

Full-Time Operators Looking For Greater Freedom + ImpactLearn how to monetize your expertise and diversify your income outside of your 9-5.

Senior Leaders (8+ Years of Experience) in TransitionAssess whether or not fractional work is the right path for your career journey.

New (&lt;6 mo) to Fractional WorkStandup your practice with confidence, clarity, and proven playbooks and accelerate the learning curve.

We're facing a purpose-crisis. The workplace and careers are rapidly changing. There's so much noise, information, and distraction. Yet, fulfillment at work matters, self-actualization is a real modern need, and knowing your WHY can get you through any setback. The key is to learn to listen to yourself, trust your own direction, and craft a meaningful career based on your priorities, passions and strengths. You’ll follow a proven 7-step framework to help you navigate change, rediscover your purpose, and design a new career path. It was created from my personal journey of reinventing my career many times, and always following my curiosity. It’s been refined through 150+ coaching sessions. This program blends&nbsp;science, spirituality and career&amp; leadership strategy&nbsp;to help you build a meaningful career and life without compromising authenticity, and wellbeing. ────────────BY THE END OF THE PROGRAM, YOU'LL... • Discover who you are: your strengths, skills, and aligned career paths.• Let go of old identities, limiting beliefs and outdated definitions of success.• Reconnect with your why, joy, intuition, and true self.• Clarify your values and confidently make decisions, and choose your next step.• Create a fulfilling career vision based on your strengths and purpose, while integrating your life and health.• Explore and tests different paths in corporate, startups, or entrepreneurship.• Roadmap your career, action plan and job searching strategy.• Get intuitive guidance on your strengths, blocks and best career paths.• Get support to find a meaningful job and switch careers, and with your LinkedIn, Resume, networking, storytelling, and interviews and more.• Explore if entrepreneurship is for you, and get personalized support on your first offer. ────────────WHAT'S INCLUDED 01 - Personalized AssessmentPersonalized report and live review to uncover your purpose, strengths, and career path using tools from psychology, Eastern medicine, and systems like astrology and numerology. 02 - Live&nbsp;LessonsLearn directly from Angelina in real-time, with teachings that blend strategy, spirituality and science. 10-weeks of guided lessons (1.5 hrs each). 03 - 1 Private Coaching CallFocused on purpose, career planning, or job search strategy. 04 - 1 Intuitive Guidance SessionAkashic Record Reading to explore your gifts, skills, energy, and potential paths. 05 - Weekly Live Group Coaching CallsGet personalized feedback, ask questions, and get support with anything going on. 06 - Resume &amp; LinkedIn ReviewSharpen your positioning based on your new positioning. 07 - Lifetime AccessReturn to the material anytime as your path evolves and get access to new materials as well. 08 - 1 Month of Drop-in SupportAttend weekly huddles after the core program ends to help you stay motivated, and make real career changes. 09 - Holistic SupportTools across mind, body, emotions, and spirit, including frameworks, meditations, and visualizations. 10 - Accountability SystemCreate an achievable plan with Angelina, and move forward with weekly check-ins and clear goals to keep you on track. 11 - Supportive CommunityJoin a cohort of thoughtful, purpose-driven peers who are also navigating change. 12 - Interactive&nbsp;FormatWork through guided reflections, exercises, and workbooks designed to help you apply the content immediately to your own career path and life. ────────────PROGRAM GOALS The goal is for you to reclaim your authenticity, reinvent yourself, find a new meaningful role, change careers or take a chance on yourself.&nbsp;Phase 1: UNDERSTAND YOURSELF AND DESIGN YOUR CAREER 01"This is where I am."Feeling lost, stuck, or pulled in too many directions?&nbsp;Understand who you are, uncover your strengths, patterns using tools across Eastern and Western personality systems (numerology, MBTI,&nbsp;etc). 02"This is what I'm letting go off."Let go of past setbacks, old identities, limiting beliefs, outdated stories of success&nbsp;and stories that&nbsp;are keeping you away from a meaningful career like financial scarcity and heal from burnout. 03"This is my true, authentic self."Reconnect with your joy, intuition and authentic self&nbsp;to&nbsp;move forward with clarity and confidence. Learn how to live and create from a place of&nbsp;balance, creativity and trust. 04"This this my deeper purpose"Through&nbsp;Akashic Records and spiritual tools, you’ll receive personalized insight into your purpose, direction, and what’s holding you back. Get clarity through intuition,&nbsp;and energy. 05"This is&nbsp;what matters to me."Overthinking? Clarify your values, priorities.&nbsp;Understand how to make decisions, use discernment, make tradeoffs on your next career steps and navigate challenges of today. 06"This is&nbsp;who I want to be"Craft a career vision&nbsp;aligned with your unique gifts, values, lifestyle and purpose.&nbsp;Learn how to&nbsp;build a fulfilling career path without&nbsp;burnout, toxic productivity,&nbsp;and self-sacrifice.&nbsp; 07"These are all the career paths I can take."Explore new career paths and possibilities&nbsp;and&nbsp;test them in real ways.&nbsp;Get&nbsp;support to&nbsp;choose the right path:&nbsp;corporate, start-up, freelancing and starting your own business. PHASE 2:&nbsp;CHOOSE A PATH &amp; ACT ON IT 08Option 1:"This is the meaningful role I'm getting."Build your career roadmap and job searching plan&nbsp;with real support on applications, resumes, networking, positioning, LinkedIn, storytelling, interviews, negotiating and more. 09Option 2:"This is the&nbsp;career change I'm acting on."Get optional support to switch careers into&nbsp;technology, Product Management, Product Design, Program Management and more based on Angelina's 12+ year knowledge of the industry. 10Option 3:"This is the entrepreneurial direction I'm taking."Define the business you will launch, that is an extension of your authentic self: your offer, audience, and marketing and sales strategy.&nbsp; ────────────Weaving Healing and Doing:&nbsp;Where Purpose, Career and Well-being Meet&nbsp; This methodology bridges the gap between inner transformation and outer expression.&nbsp; Where most paths separate wellness, purpose, and career, this approach integrates them so you don’t just feel better, you create a life and career that's more in tune with who you are. It guides you through the full experience I've personally gone on and vetted through 150+ coaching calls:&nbsp;from healing mental and emotional patterns and reconnecting with your WHY, to discovering what you’re here to offer and&nbsp;acting on a career plan that matches your authentic self. Rather than chasing success blindly, bypassing your needs or acting from burnout, you'll learn to act from balance, flow and creativity. We'll use real frameworks that turn all of your personal discovery and insights into real action in your life, career, or other creative and entrepreneurial paths, all with support from wellness and spiritual techniques.

The only coaching program that turns self-discovery into real action and results

Live Group Coaching Calls

Tuesdays

Your 1-hour Private Intuitive Coaching Call

Week of September 22

Your 1-hour Private Career Coaching Call

Week of October 27th

Optional: Themed 1-hour long workshops

Optional Thursdays

Course Schedule

💼&nbsp;Navigating a layoff, setback or career break, and&nbsp;ready for intentional growth, clarity, and to take your next step.

🔄&nbsp;In a role or career you've outgrown, feeling drained, stuck, or demotivated and ready to&nbsp;find your purpose, and a meaningful&nbsp;career path.

🌱&nbsp;Already have a direction in mind, and want accountability&nbsp;to make it a reality&nbsp;as you pivot careers,&nbsp;job search, or start something.

🔥&nbsp;Burnt out from hustle culture or toxic environments, and want to reconnect with your authentic self, intuition, and confidence.

⚙️ You’re worried that AI or automation might replace your role, and you want to discover new career paths, and future-proof your career.

Understand yourself, purpose, career and leadership using tools like MBTI, Enneagram, and numerology.

Understand yourself, patterns, strengths, gaps and career paths

Release past setbacks, old identities, limiting beliefs, outdated stories keeping you from a meaningful career.

Let go of anything stopping you from a meaningful career

Learn who you are, outside of work identities, trust your inner voice, and move forward with confidence and creativity.

Reconnect with your why, self, joy, and intuition

Understand why you're feeling stuck, demotivated or burnout and learn how to navigate tricky work situations, so you can set yourself up for success.

Navigate career setbacks, layoffs, difficult work situations

Stop overthinking, learn to make decisions, navigate tradeoffs, and take meaningful steps forward.

Clarify your values and priorities

Get support to match your strengths, past experiences, and passions to meaningful career paths and roles.

Explore and test new career paths 

Get guidance into your purpose, direction and what's holding you back.

Get intuitive guidance and personalized insights

Craft your career &amp; life vision based on your values, strengths, and lifestyle without burnout, toxic productivity.

Design a fulfilling career vision and roadmap

Design a practical career and learning plan to transition into a new role in tech, business, or a creative path.

Identify your skills, and gaps

Get support on resumes, LinkedIn, networking, interviews, applications, positioning, and more.

Create a plan to job search or switch careers

Define the business you will launch, with a unique offering, audience, marketing and sales plan, and prototype.

Explore if starting a business is for you

Feeling stuck in your career or purpose? Reconnect with who you are, discover your why, design your ideal career and life, and take action.