Trust Enablement

Improving Sales Performance with Enablement Recruiting, Consulting, Outsourcing, Coaching, and Insights on Strategies, Tactics, and Tools

Trust Enablement Sales Enablement Job Seeker Program

Why Join Our Free Program?

Are you an unemployed sales enablement professional looking for your next role?

The team at Trust Enablement is here to help during this challenging time.

Contact us to learn more and take advantage of our FREE Enabling The Enablers Job Seeker Package.

You will receive:

  • Access to our weekly mastermind sessions.
  • Free access to our communication workshop – coaching on storytelling for enablers, interview practice, and more (a $500 value).
  • Job seeker connection support – we will ensure the right hiring managers know you’re available, increasing your odds of finding the right next job.

We are committed to supporting the unemployed enablers through these challenging times.

In addition to our free program, check out the tips and guidance on this page to help you navigate your job search.

Complete The Sign-Up Form

Community Feedback On The Program

John and the Trust Enablement team have been stellar in providing current insight, best practices and guidance in the field of Enablement.  Their services, such as weekly Job Seeker Mastermind, Story Telling Workshop, weekly Enablement Newsletter, CRO Perspectives, etc. have all been purposefully designed and delivered to up-level your enablement skills and understanding of the latest trends in the marketplace.  John’s work has effectively created a worldwide community of enablement professionals who are better equipped to effectively re-entering the marketplace with a maniacal focus on delivering business results.

Rodney Umrah

Getting Started – The Unemployment Journey

Shauna MacNeil, a long-time enabler and wonderful human being, stopped into one of our weekly masterminds to share this advice with the group.  We have included it for your benefit.

Give Yourself Grace, But Then Move On
You are entitled to a short period of grief over losing your job.

Take a day or week to deal with this, heal yourself, and prepare for the job hunt.

But, then move on.

Get outside, set a schedule for yourself, create a to-do list, track your progress, and avoid the trap of unplanned time.

Don’t Go Solo

Join a community like our Job Seeker Program and/or hire a coach.

Maintaining connections, building a growth mindset, and learning new things will keep you sharp, focused, and in the right mind.


Network for job openings to gain new perspectives on the journey, learn from others, and reconnect with others.

Note: Build this into your annual career plan. Every year, make a point to connect with 5-6 people and build a real professional connection. Or, get more aggressive, choose 2-3 people each month, and grow your network with genuine relationships.

Own Your Story

Unfortunately, many people enhance or lie about their experiences on their resumes.

Don’t do this.

But, understand and own the positive accomplishments in your career story.

And, if you need help with this, join our program; we’ll help you see what you have accomplished and tell your stories honestly and with impact.

What’s Your Elevator Pitch? 

Take the time to develop a crisp elevator pitch that, like your enablement success stories, should follow a clear arc:

  • Why do you do what you do?
  • How do you accomplish your why?
  • What results do you deliver?
Know What You Want

What are your non-negotiables?

Consider items like salary, title, work location/hybrid remote, scope and responsibility, where you report in the org, what you want to do, and so on.

Prospecting for Job Seekers

Chantae Sheetz is collaborating with Trust Enablement to share regular advice for job seekers.  These prospecting tips come directly from her.

Get crystal clear on a few things:

  • Values – if you haven’t assessed your personal and professional values recently, there’s no better time than now. What do you value, and what do you want your future employer to value? (not sure where to begin?! Direct Message Chantae on LinkedIn if you want to go through the Values Exercise.
  • Role – What kind of role aligns with your strengths and passions that brings you the most joy? Is it what you’ve done before, or will you try something completely different? Where do you see yourself in 5 or 10 years? – Work backward from that future version of you! 
  • Company – What size of a company is your sweet spot? Are you a start-up gal/gent? A large Fortune 100 gal/gent? How many people are on your future team, in your department, etc.? What is your boss like? What is your CEO like? Who are their investors if they’re private? Who’s on the board? What benefits do you require? What kind of diversity do you want to see? What kind of ERGs do they have? Recent news? Product market fit? Where do you see the company in a few years? Remote/in-person/hybrid? (you get the point)
  • Targeted Salary – This one… I CAN’T stress this one enough. What happened to you sucks, AND the last thing I’d ever want for anyone laid off is to take any offer they get because they get caught in their head. Know what you want, don’t go backward in your salary, AND negotiate that ish when that time comes (more on this in a future post when we get to “sign your offer!!!”)
  • Time – How much time can you commit to your job search while maintaining positive mental health and wellness? Be realistic with yourself (include job searching/applying, interviews, interview prep/research, follow-up communications, networking calls, mock project creation, etc.)

Ok… it’s essential not to skip steps. Once you’re clear on those things, you won’t be throwing spaghetti at the wall or mass “spray and praying” your resume to every open role you see. Like in sales, you don’t reach out to anyone for funsies; you must first know WHY and the desired outcome.

Chantae suggests taking an account-based approach to your job hunting at this point.  She notes that she likes to have 3-5 target companies that are her DREAM companies. They align with her values, mission, and purpose and are a product fit that FIRES her up!

When you identify these companies, what should you do? This will look very similar to a target account strategy in sales.

  1. Set up news alerts. You want to be notified of any recent news updates they have. (Funding, leadership, hiring, givebacks, etc)
  2. Identify a handful of critical employees you resonate with, are in the org you want to join, would be cross-functional partners, or can be champions for you through the interview process.
  3. Do deeper company research than with other companies you’re applying for. (For example, if they’re public, read their 10k or investor reports, how is the role you’re applying to help them achieve their company objectives and what VALUE can you drive and add to their organization) *** Hint, do 10ks intimidate you a bit? Throw it in ChatGPT and ask it to summarize it for you.

That’s great, but what do you do with all this research?

Find a personalized way to nurture and add value to the contacts you’ve identified, anyone who is a leader or above, reach out to with targeted messaging directly speaking to bullet #3.

Invest in Your Professional Development

Sales Enablement professionals put everyone else first and often fail to invest in ongoing professional development.

This lack of investment in yourself hurts your job performance, job hunting, and mental health (breaks are necessary).

How can you invest in yourself without breaking the bank?

  • Read our Ultimate Guide to Sales Enablement.
  • If you are unemployed and part of this program, you get free access to all our events.
  • If you are employed, join our low-cost, high-ROI events (only $50) and workshops (only $25).
  • If you are employed, get a qualified enablement coach — while unemployed, join our program and get lots of free coaching.
Invest in Updating Your Resume

Many people fail to keep their resumes updated, ATS-friendly, and well-designed.  It’s not usually a priority until…  Well, until it is…

And, Indeed offers resume writing/editing services, which you can learn about here.  As of the time of this writing, pricing is:

  • Recorded review + notes = ~$35
  • 20m coaching session = ~$70-100?
  • Professional write or re-write = $200-250?

And one enabler told me the recorded review was the best $35 they spent!

Develop Your Enablement Portfolio

In competitive job search markets (like we find ourselves in right now), companies often ask enablement professionals for examples of their work–their enablement portfolio.

Our good friend, Sam Moody, was kind enough to share a templated Enablement portfolio.  Download the Sales Enablement Portfolio.

Courses and Certifications

Check out all of these resources:

Other Resources We Recommend

Here are additional resources that job seekers need to check out.

Applying But Not Getting Interviews

This video provides eight great tips to overcome this problem. The only tip we don’t recommend in this list is to create a custom resume for each job application.  The ROI isn’t there, in our opinion.

Telling Your Success Stories

Review the following storytelling frameworks:

Your process for these stories should look something like this:

  • Identify a project you worked on that you are proud of, one you would generally love to share in interviews or with peers.
  • Ensure you understand WHY this project took place, the business KPIs you attempted to influence, and how it helped your peers, leaders, and teammates.
  • Craft your story across these elements.
    • What was the problem you were trying to solve?
      • As any great seller would do, focus and wallow in the pain to the business and the people in the business.
      • Go deep into the business and personal pain, using examples.
      • Be clear — why did this problem matter in terms of business KPIs.
    • What did you do?
      • What did you do?
      • How did you work with others?
      • Be detailed here, but don’t dive into the weeds.
      • Always tie actions to how they were helping overcome the pain and achieve business impacts.
    • What happened?
      • Tie the impact of your program back to the problems you were trying to solve and impact the KPIs.
  • Practice and get feedback.
    • If you have friends or peers you can practice with, do so.
    • Join our free program if you are unemployed.
    • Register for our paid coaching program.

Interview Questions to Ask Hiring Managers

If you are a sales enablement professional looking for work, how do you know if the company you are interviewing at understands enablement?

How do you know if their vision is aligned with yours?

One key method?  Asking great discovery questions during the interview process.

That is why we are working to gather, update, and extend the following list of questions.  Note: Matt Cohen has generously shared the first ten questions.

1. Does enablement report to the CRO? (Enablement typically falls under the CRO, Growth, RevOps, or Marketing. Reporting says a lot about how the strategy will be shaped.)

2. How many employees are in the audience Enablement supports, and how many are planned to be on the Enablement team within the next couple of quarters? (Is the support ratio out of hand? Are there plans to address with hiring?)

3. How are you getting your sellers’ messaging to meet the buyer where they are? (How customer-centric the organization is since that will inform Enablement’s ability to impact revenue.)

4. Are you at a point of growth and scale? Is business closing exponentially and hiring increasing? (Enablement fit)

5. Tell me about key enablement projects for last quarter and how the CEO and most senior enablement leader, e.g., CRO, have been involved. (Leadership fit and exec sponsorship)

6. How do you define Enablement? (This is the most important one. They will most likely be wrong unless they have a background in it. Are they receptive to your definition?)

7. What is Enablement’s audience? (Fine if it’s still at the phase of being just sales, but it’s good to see if there is a willingness to expand in the future.)

8. What are the biggest challenges you see Enablement solving in my first quarter on the job? (Their answer will show whether they consider the role more strategic or tactical. Do they give you all the answers or leave room for you to figure it out?)

9. How do trust, empowerment, and autonomy play a role in the culture? (This will tell you how much they are willing to allow someone specializing in a function to own it.)

10. What makes me a good fit for Enablement at this company? (Did they take the time to review your background? Do they know enough to connect your skills to what enablement should be working on?)

And here are a few more:

11. How long has this role been open?

12. Where have other candidates fallen short of your needs?

13.  How urgent is it for you to fill this position?  What’s driving this need?

Our friend, Crystal Nikosey, and other enablement professionals have also crowdsourced a great list of questions in this Google Document.

What Interview Questions Do Senior Enablement Leaders Ask During Interviews?

Review this wonderful thread where enablement leaders share their favorite questions.

Are you looking for other Interview questions?

This site includes a categorized list of 800+ interview questions.

Preparing for Panel Interviews

Example Projects to Support Your Interviews

These are being shared as examples by members of the Trust Enablement Job Seeker Program.

Presentation Walking Through an Example Training Program – Contributed by Thao Vy Lengo
Basic Pitch Deck Example – Contributed by Thao Vy Lengo

When Rejection Happens

You will get rejected sometimes, even if you do a fantastic job in the interview process.  

Someone else may have been slightly better, had more chemistry, or asked that one question that made the difference.

When it happens, remember:

  • Use it to improve.  Ask the hiring manager, if possible, what you could have demonstrated to make hiring you a no-brainer decision.
  • Use it to build your network.  Ask the hiring manager and others you connected with to connect with you on LinkedIn.  Let them know you appreciate their time and want to stay in touch.

Where Should I Look For Enablement Jobs

Our friends at GTMBuddy are investing time and money to capture and spotlight every open enablement job they find (and it’s an extensive list).  We have included the live feed below — we recommend you check out their job listing page.

In addition to this fantastic resource, check out: