Location: Chicago, Illinois. Employer listing checked: November 14, 2026.
Asana’s Chicago Customer Enablement Manager role focuses on helping enterprise customers adopt workflows and improve the way teams work. It combines discovery, facilitation, training, and follow-through. The posting calls for at least four years of relevant customer-facing experience and describes an office-centric hybrid schedule with Monday, Tuesday, and Thursday as standard in-office days.
The work starts with behavior, not training attendance
A customer may ask for a training session when the actual problem is that projects start without an owner or that approvals are scattered across messages. A useful enablement engagement starts by observing the current workflow and deciding what should change. Training then supports the behavior instead of becoming the only success measure.
An enterprise account can include sponsors, managers, champions, and end users who need different information. A sponsor may want visibility into cycle times. A manager may need consistent intake. End users may want fewer duplicate updates. Show how your discovery process gathered these needs and selected a manageable first use case.
Prepare an adoption case study
Pick a rollout where the original workflow created an observable problem. State exactly what people were doing before your intervention and how you learned that it was a problem. Then describe one change, such as a new intake process, handoff, template, or review cadence. Explain how you helped the customer test it with a small group before the broader rollout.
Report a result that reflects behavior. Examples include a greater share of requests entering through the agreed channel, fewer projects missing an owner, or less time spent duplicating status updates. If you have attendance numbers, pair them with something people did differently afterward. Explain how you accounted for temporary spikes around launch.
Practice facilitating a difficult workshop
A useful practice scenario involves managers who want visibility and team members who worry about added overhead. Begin by asking each group what decision it cannot make today. Set an example workflow on the screen and agree which fields should be required. Invite a representative to run a realistic task in the workflow, and record points where the process is confusing.
Close the scenario with a decision and a follow-up plan. Define the initial group, who can answer questions, and when you will review the outcome. Describe how you would respond if adoption was low after two weeks. Look for whether the workflow is hard to use or fundamentally mismatched before recommending more training.
Explain your commercial awareness
The posting connects enablement with retention and expansion and expects collaboration with Customer Success, Sales, and Services. Prepare an example where you informed the account team of an adoption risk early. Explain what evidence supported the concern and what owner took the next action. If you identified an expansion opportunity, show how it followed from demonstrated customer value rather than activity alone.
Build an application around evidence the reader can verify
Start with a customer rollout where people kept bypassing an agreed intake process. Draft three sentences before writing a résumé bullet. The first explains the problem in language a colleague outside your team would understand. The second states the decision you owned and why you chose it. The third gives the result and identifies what you know firsthand. If the outcome came from several people, say which part you can explain in detail. This exercise helps turn a broad claim into evidence you can discuss if the employer asks follow-up questions.
For this opening, consider preparing a short engagement plan linking discovery, a workshop, and follow-up. You may use it to organize your interview answer even if you never send it. Include only information you are allowed to share. Replacing company names is insufficient if a chart or a unique deal detail still identifies the organization. A reconstructed example with synthetic data can show the process if you label it clearly and avoid presenting its figures as a past result. Give each entry a short caption that explains the decision it supported.
Review your story against workflow participation, completion of core tasks, sponsor feedback, and unresolved barriers. Decide which facts are essential to understanding the work and which are background. A useful test is to describe your role in one minute, then ask someone to repeat back the problem, your contribution, and the outcome. Revise any part they cannot follow. After that, prepare a longer version that makes room for constraints and trade-offs without obscuring the main point.
Interview practice with a role-specific prompt
Practice question: How would you determine whether a workshop changed how the customer works?
A sponsor wants every team onboarded at once, but a pilot reveals inconsistent intake rules. Explain how you would limit scope without losing sponsor support. Choose a shared request type that crosses only two teams and define what a completed handoff looks like. Present the pilot as a way to learn quickly and reduce rework in the larger rollout.
Build a second answer from your own work or studies. A useful starting point is a situation where your audience completed training but returned to an older workflow. Explain what made the situation difficult and what information you had at the time. Then describe your reasoning, including whether an action like observing where the newer process created extra steps and piloting a simpler version would have made sense. If you made a different choice, explain the constraints. The goal is to show how you evaluate alternatives, make a decision, and learn from the result. A mixed outcome can be useful if you can account for it honestly.
To prepare follow-ups, review a baseline, the revised workflow, and a review of usage after the pilot. Think about what each piece would verify. Interviewers can ask how you established the baseline, what happened when an assumption changed, or how you knew the project worked. If you do not have reliable numbers, identify something observable you can explain, such as a completed handoff, a passed test, or a change in the expected workflow. Keep a clear distinction between the facts you observed and the conclusions you drew from them.
Decide whether the opening fits your priorities
One question to ask the employer is: “Which adoption metrics does the enablement team share with customer success?” Listen for an answer that gives examples, such as the first assignment, the people who will review your work, or the outcomes measured during onboarding. Make a note of anything the listing leaves open about location, work arrangements, availability, or the scope of the position. A written requirement on the official posting deserves more weight than an assumption based on the title alone.
Before submitting, read through the application as if you were the reviewer. Put the most relevant evidence where it can be found quickly. Check that job titles and dates agree across your résumé and application, that every link works without credentials, and that the selected draft names Asana correctly. Use the JobCraft AI résumé checker to review your document against the full posting, then make edits based on work you can demonstrate.
Official listing and application
Confirm the opening is still listed and follow the employer’s submission instructions. View the job and apply through Asana
