Portland Career Coach, Kate Cockrill

Career Transformation

Have you decided that something about work needs to change?

When you are 15-or more years into your career, change can take many forms. Most folks are familiar with vertical changes such as job promotions or horizontal changes like moving into a new department or to the same job at a new company. However, I specialize in the career zigs and zags that can be harder to define and navigate.

  • Career redesigns where you shift your current responsibilities and even job title in substantial ways to add more value to your business or organization and account for your own work style preferences.

  • Second (or third) careers where you apply your current skills and/or possibly retrain so you can bring your unique brilliance to a whole new industry, movement or community.

  • Going Solo(preneur) where you take the skills you’ve accumulated in your career, combine them with your passion for helping others and start your own business.

  • Career TBD where you admit to yourself that you still don’t know what you want to be when you grow up… but you also know there is something important for you to accomplish in this lifetime.

Navigating a nontraditional terrain can be a lonely adventure. You may need to keep your plans under wraps while you work out the details. Your mentors and network may not have relevant advice for your new direction. Your spouse or partner may be supportive…but concerned about how your changes will affect your life & family.

How can you maintain focus on your goals in the face of these odds?

Topics include: career transitions management, career redesign, pitching and networking, salary negotiation, effective resumes, burnout prevention & recovery, personal productivity

Option 1: Design a Career You Love

Are you ready for the kind of coaching that can make your career dreams a reality in just two months?

Career Design is a process that I have iterated over hundreds of hours of career coaching – to help my clients identify and achieve their career goals. This program puts your needs and experiences at the center of the career change process and then finds solutions that work for your skills, experiences, interests and goals.



ReflectExperienced professionals aren’t starting from scratch, you are starting from well…experience. We will explore your career peaks and valleys, to produce a personalized user guide detailing your work values, skills and assets and ideal work environment. Why? When you know yourself, you attract better and more satisfying opportunities.



EnvisionDo you want to start a local cafe or write a best-selling book? Lead a design team or launch a business consulting co-op? Great visions are specific & motivating. They help us take calculated risks and say ‘yes’ to valuable opportunities. We will generate a compelling vision so that you can clearly communicate your career destination to the world.




Career journeys are especially prone to breakdowns and detours. When you don’t know the way and there is so much to do, it’s easy to get lost. Drawing on your user guide and vision we will create a life & career roadmap specifying goals, strategies & milestones. Map in hand, you can experience the freedom of travel without going off course.



BuildNow, let’s set you up for success! When we’re making big changes, we tend to fixate on big results while resisting important small steps. We will build a personalized toolbox of habits, tactics and systems to support productivity, decision-making & communication. You will be able to make strides now and sustain yourself later in a career you love.




Does networking make you cringe…even though you KNOW you need to do it? Networking confidently through career change takes two things: 1) forethought and 2) practice. We will compose a compelling career pitch featuring your experiences, assets, vision and goals. Through practice (hello role-play!) we will bring ease to networking.




Why postpone your pleasure until after you have achieved ALL of your goals? Designing a career you love is about building appreciation into each moment. Sending a book draft to your publisher, Signing the lease on your new cafe, Greeting your new team or forming a new business partnership. We will celebrate each win of your journey so that you can thrive now in the career you’re designing.


Package Includes:

  • 8 1-hour private coaching sessions (taken weekly or bi-weekly)
  • 8 personalized session summaries with access to additional resources (eg. podcasts, articles, books, video tutorials)
  • Resume & Linked In Review & Feedback
  • The Design a Career You Love workbook
  • Customized homework assignments for each step of the journey

Package Cost: $2500

“Before starting working with Kate, I felt overwhelmed, stuck, hopeless, and fairly well tapped-out for future growth. A major turning point in coaching with Kate was the concept of “Ethical Marketing” which gave me the direction to feel confident in presenting myself in the best way possible.”

Sharon Gan, Workday Student Consultant

Sharon Gan

Option 2: Perfect Your Career Pitch

Talking to other people about your career change goals – with ease and clarity – is the most important skill for finding new work that you will love. A great career pitch can help you learn about new opportunities and make that will make your career goals a reality. Including:

  • New jobs.
  • Contracts.
  • Strategic partnerships.
  • Start-up capital.
  • Grants.

My most practiced pitches have generated concrete opportunity and resources like:

  • Grants: Over two million in funding for the nonprofit I founded in 2013.
  • Contracts: A $90,000 contract for my consulting business in 2019.
  • Partnerships: The opportunity to train with a Fortune 100 company this past year.

Are you afraid of talking about your new direction  – for fear of looking stupid, communicating uncertainty or rambling on without saying much.

My Perfect Your Career Pitch session is one of the most fun and rewarding sessions I offer in my “Design a Career You Love” coaching program because in one hour it helps them to::

  • Tell a succinct and engaging story about themselves;
  • Talk authentically and persuasively about their career goals;;
  • Get off their computer and into the world so they can make real things happen for their careers;
  • Find and land great jobs, contracts and partnerships.

Package Includes:

  • A 1:1 90-minute private coaching session;
  • My “Perfect Your Career Pitch” workbook;
  • A custom report on your areas of strength and growth so you can deepen your practice.

Package Cost: $199

Perfect Your Career Pitch Career Pitch
Jasmine Agnor

“Make the investment in yourself, make this experience the best it can be. Kate is really good at asking the hard questions, and pushing me forward to get to that next place, level, and insight. Her active listening skills as well as her ability to integrate my experience and synthesize it in a way I can go back and use it in the future was really helpful.”

Jasmine Agnor, Industry Marketing Manager

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