Trust Enablement

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

Enablement Job Seeker Tips

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.

On-Demand Webinar – Job Search Strategies for Sales Enablement Professionals

Our friend, Natosha McIntyre, delivered this fantastic webinar for a few of our job seekers.

The PowerPoint Natosha used for this webinar can be found here.

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?

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!

ATS Friendly Resume Resources

When you work on your resume, ensure it will get by the algorithms used by applicant tracking systems (ATS) by following the advice in this article.

Here are a few low-to-no-cost technologies to help keep your resume ATS-friendly:

Beautiful Looking Resume Resources

This website, Visual CV, does a beautiful job of creating a good-looking resume.

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:

Recommended Coaching Resources

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

Other Resources We Recommend

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 excellent 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.

10 Challenging Interview Questions and How to Respond

Our friend, Natosha McIntyre, shared this section with us to share with the community.

1. Share a Personal Career Highlight

Interviewers ask this question to understand your achievements and strengths. Consider discussing a project where you exceeded expectations, received recognition, or solved a significant problem. Emphasize your impact and how it aligns with the job you’re interviewing for.  Sample Answer: “One of the proudest moments in my career was when I led a cross-functional team to launch a new product ahead of schedule and under budget. This project not only showcased my leadership and project management skills but also resulted in a 30% increase in revenue for our company within the first quarter of its release.”

2. What Sets You Apart from Other Candidates?

To stand out, highlight unique skills or experiences. Mention specific accomplishments that demonstrate your qualifications. For example, if you’re applying for a project management role, discuss how you successfully led a cross-functional team to complete a project ahead of schedule and under budget.  Sample Answer: “What sets me apart is my ability to combine technical expertise with strong communication skills. For example, in my previous role as a data analyst, I not only conducted in-depth data analysis but also translated the findings into actionable insights for non-technical stakeholders, which led to more informed decision-making.”

3. Explain a Complex Technical Concept Simply

Choose a complex term from your field and simplify it for a non-expert audience. For instance, if you’re a software developer, you could explain “algorithm efficiency” by comparing it to finding the fastest route on a map. Relate the concept to something relatable and easy to understand.   Sample Answer: “Consider ‘neural networks’ as virtual brains for computers. Just like our brains learn from experiences, neural networks learn patterns from data. They have layers, like our thinking process, where each layer processes specific aspects. Together, these layers help computers recognize patterns and make predictions, like identifying objects in images or translating languages.”

4. Share Your Strategy for Career Growth

Outline your career aspirations and explain how you plan to achieve them. For instance, if you aspire to become a data scientist, discuss your commitment to ongoing learning, online courses you’ve completed, or projects where you applied new data analysis techniques.  Sample Answer: “I’m committed to continuous learning and growth. Currently, I’m pursuing online courses in machine learning to enhance my skill set. I also seek out challenging projects at work that allow me to apply new skills and take on leadership roles, helping me move closer to my goal of becoming a senior data scientist.”

5. Describe a Time You Adapted to Change

Share a scenario where you adapted to a significant change, such as implementing new software or adapting to a remote work environment. Highlight your flexibility, problem-solving skills, and ability to positively influence others during transitions.  Sample Answer: “When our company transitioned to remote work during the pandemic, I quickly adapted by setting up efficient virtual collaboration tools, organizing regular team meetings, and providing resources for team members to cope with the change. This ensured productivity remained high despite the challenging circumstances.”

6. Discuss a Project That Required Collaboration

Describe a project where you successfully collaborated with colleagues. Discuss how you communicated effectively, resolved conflicts, and contributed to the project’s success. Highlight specific examples of teamwork and its impact.  Sample Answer: “In a recent project, I collaborated with a diverse team from various departments. While the technical aspects were essential, what made it successful was the strength of our human relationships. We fostered an environment of trust and open communication, valuing each team member’s contributions. This synergy not only led to a streamlined process but also forged lasting professional relationships that continue to enhance our collaborative efforts.”

7. How Would You Handle a Difficult Client or Colleague?

Provide a hypothetical scenario and outline your approach to resolving the issue. Discuss active listening, empathy, and problem-solving. For example, you might mention how you would address a client’s concerns, propose solutions, and maintain a positive working relationship.  Sample Answer: “If a client or colleague were upset, I would first actively listen to their concerns to understand their perspective. Then, I would propose solutions, emphasizing our shared goals. By demonstrating empathy and a commitment to resolving the issue, I believe we can find common ground and maintain a positive working relationship.”

8. Explain a Complex Term in Layman’s Terms

Choose a complex term or concept from your field and simplify it. For instance, if you’re in finance, explain “asset allocation” as the strategy for spreading investments across different types of assets, like stocks and bonds, to reduce risk.  Sample Answer: “Let’s break down ‘quantum computing.’ Think of traditional computers as people searching a massive library page by page, while quantum computers are like instantly knowing the right page without looking through the rest. They use ‘qubits’ instead of ‘bits,’ allowing for incredibly fast calculations and solving complex problems that were once impossible to tackle with classical computers.”

9. Discuss Your Approach to Ethical Dilemmas

Share a personal or hypothetical ethical dilemma you’ve faced or might encounter in your field. Explain your ethical principles and decision-making process. Highlight your commitment to honesty, integrity, and ethical behavior.  Sample Answer: “In my previous role, I encountered an ethical dilemma related to data privacy. I prioritized transparency, informed all stakeholders, and sought legal advice to ensure compliance with regulations. Upholding ethical standards and integrity is non-negotiable for me, even if it involves difficult decisions.”

10. What’s Your Vision for the Future of This Industry?

Discuss industry trends and your vision for its future. For instance, if you’re in healthcare, talk about the importance of telemedicine and how it can improve access to healthcare services. Demonstrate your knowledge of the industry’s direction and your enthusiasm for contributing to its evolution.  Sample Answer: “I believe the future of our industry lies in harnessing the power of artificial intelligence and automation. By integrating AI-driven solutions, we can enhance efficiency, reduce costs, and provide more personalized experiences for customers. I’m excited to be part of this transformative journey and contribute to shaping its future.”


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.