Pivot Coaching Monthly Retainer

If you landed on this page, it means you are part of the Pivot Coaching inner circle! We are very selective about who we work with for ongoing coaching beyond the Pivot Jumpstart sessions, and are thrilled to offer you a spot in our monthly coaching program. We focus on fewer clients so that we can make the most out of every partnership.

When you sign-up for ongoing monthly coaching, we will become your number one supporter and we will go to the mat for you to ensure that you’re moving in exactly the direction you want. In return, you’ll commit to doing the work, even when it gets hard, and to making the changes you need to make so that you can operate from a place of creativity, strategy, and ease.

The strength of our relationship will play a key role in your progress. It has been proven in study after study that the relationships between mentor and mentee, counselor and client, doctor and patient, teacher and student and coach and client have a significant impact on results.

We will do everything we can to support you by getting to the heart of what you want, challenging you to go further than you think you can, providing tools and resources to make it easier, and putting you in touch with people who can help you. We'll be an open book and you can ask us anything, whenever the need arises. We will provide encouragement and ideas around your next steps, and we’ll be there to dish out a healthy dose of tough-love if we think you’re holding yourself back. Just knowing that we're looking out for you will play a big role in how far you’ll go.

How It Works: Our Process

The phases below describes a general idea how we will work together, while also making room for any surprises that may pop-up on any given call. For example, we may be laser-focused on your career or business, but when relationship or health issues surface we can absolutely take a time-out to help you get clear there first.

We will work through the following three major phases, then repeat each time we set new goals (but condensed each time since we will already have established a strong base of trust and rapport):


1. Discovery & Jumpstart—The jumpstart sessions and prep questions will help us get to know you better and make quick progress on some of your short-term goals, while keeping your broader strategic vision in mind.

2. Set the Foundation: Values—During this phase we will define what success looks like, we’ll dig deep into your values and we will make sure your life, business and quarterly milestones reflect what is most important to you.

3. Vision and Desired Outcomes—We will also set clear deliverables for our time together each month, so that we both know what we’re working toward, and so that you get your money’s worth and then some! 


4. Strategy—Once we are clear on the desired outcomes for our coaching, we will create a high-level strategy for the career and business outcomes you are looking to achieve, keeping your personal goals in mind as well.

5. Prioritization and Milestones—Once we know at a high level what you are looking to achieve for the next three to six months, we will prioritize what is most important from session-to-session, and look toward where you should focus your attention next. We will send helpful templates, tools and resources in-between calls to provide helpful shortcuts wherever we can.

6. Team Support—We will brainstorm who will be critical to have on your team, and how to best delegate and define those roles. For any areas we don’t have the expertise to cover, we will brainstorm who you can reach out to (and provide connections to our network where it makes sense) for information, mentorship/support and even help doing the work.


7. The trenches—This is where you really dig into the trenches of doing the work. You will be trying things out, testing ideas and making things happen. Oftentimes clients see progress much sooner than they expected, but only after spending some time on the big picture vision. This is where all the vision and big ideas really get road-tested, and we will check-in frequently to ensure that you feel great about the direction you’re heading and the progress you are making.

8. Surviving (and learning from) the dips . . . and celebrating successes—When challenges arise we will make a plan on how to deal with them, and you will continue to move through the obstacles that may have stopped you in the past. We will determine when it makes sense to pivot, course correct or keep charging ahead. And what kind of coaches would we be if we didn’t help shout your praises from the mountaintops?! We are often so quick to move on once we achieve successes (big and small), part of our work together will be to slow down and appreciate all the great things you are doing so that more will follow.

9. Planning what’s next—Every six months, we will revisit your long-term strategy and cue up the next set of major milestones. We will review what we have accomplished so far, and look for any learning or systems optimization that we can implement for the next round of projects.



  • When you sign-up for ongoing coaching, you will be billed on the first of every month and can cancel at any time. This helps keep you and your coach motivated to make the most out of every month! You will check in at regular intervals to set new strategic goals and ensure that you're making the accelerated progress you desire.
  • There is no minimum commitment of three or six months (as many coaches have), though we do recommend entering this relationship with a longer-term vision in mind. Some of our clients work through their goals in three to six months, others have been with us for years, adjusting their goals and setting new ones each time previous milestones are accomplished. 



  • You will pick a recurring day and time with your coach for sessions; that way you can set it and forget it (and move sessions on a one-off basis as needed. 
  • We respect your time (and hopefully vice versa!) and will make sure our sessions start and end on time. If you need to cancel or move a call, please email at least 24 hours in advance. Less than 24 hours notice means you need to find a way to make it to the call or forfeit that session.
  • Rescheduling: Given that the retainer format is on a monthly billing cycle, our sessions cannot be rescheduled beyond the month they are slated for (but we can certainly email in lieu of the call if you are unable to make it). Stretching one “month” of consulting over five or six weeks is not an option.


Other notes and tidbits about our Pivot Coaching Style

  • Our sessions are 100% confidential. This is critically important to us so that you have a safe space to talk about whatever is on your mind. We will not tell people we are working together without your explicit permission, nor will we ever share the content of our conversations, though you should feel free to discuss or share whatever you feel comfortable with outside of coaching calls. We may sometimes refer to anecdotes and stories from past clients who have been through what you have and overcome it. Using stories in this way helps you better understand concepts and lets me demonstrate situations so you can learn what you need to know. Rest assured that key details are so far removed from reality that recognizing actual people and/or their issues would be impossible. Names remain confidential and are always protected for privacy.

  • You will set the agenda. Although the first two Jumpstart calls are often more directed by us, we will start the remaining sessions by asking what you hope to walk away with by the end of each one. It would be great for you to put some thought into this before we meet each time, and we will come with my own ideas and suggestions too. Sessions will often take a natural evolution, so there will be no pressure to stick to that agenda. It's just nice to have a session-by-session vision of success and a place to start.

  • We may ask stupid questions or "blurt" something out if we get a gut instinct related to something you've said. However, we are 100% completely willing to be wrong. We will learn as much from your correction as from our question (if not far more).

  • 10,000 foot view: We may interrupt you or ask you to "bottom line" if we are getting too far into story or details—the best way (by far) to maximize our time together is to focus on the big picture: where you are now, where you want to be, and what you are learning about yourself because of those details (without going too far into the story behind them).

  • We are very open to feedback. If something is not working for you or you wish we could go in a different direction, please let us know! This is all about you—help us make sure we make the most of our time together. We want to empower you in this relationship and make sure that you are getting everything you want from it.

  • Ask us anything! Seriously, no question is off limits. We are happy to share our own thoughts, experiences, and failures to the extent that it is helpful to you. That said, we always encourage and will give a bias to your thoughts and opinions first—it reinforces the idea (and truth!) that you are the expert on you and your life. Your gut instincts trump ours! Once we've explored your thoughts and reactions first, we are happy to chime in toward the end of the call. Sometimes clients also want to dedicate an entire call to a Q&A format about our career choices and/or businesses — that’s great too! Just let us know when we jump on the phone :)

Ready to Enroll in Monthly Coaching?

If so, awesome!! We are thrilled to continue working with you :) 

Let your Pivot Coach know, and keep your eye out for the first invoice (sent from Jenny) on the first of the month for whenever your ongoing coaching is set to begin.