Skip to content
CV Rocket
Get started
How it worksThe enginePricingBlogContactSign in

Open nowPosted 27 hours ago

Director, Member Services Operations

When5 open roles

Pay
$150,000 – $170,000 a year
Where
USA
Work mode
Remote
Get the CV for this job

From $25 per CV, paid once. No subscription.

Your applicationOpen nowDirector, Member Services OperationsWhen · USA

  1. YouYes, apply to this one.

  2. CV RocketCV written for this posting.

  3. 25 readersRecruiter, hiring manager, skeptic. Round after round.

  4. CV RocketApplied on When's own form.

The reply lands in your private mailbox

3×more interviews than doing it yourself with ChatGPT.

The clock on this job

Early applications get read.

13.6% of postings close within 7 days. Measured by our own scanner across the market. When postings stay open a median of 12 days.

Share of postings closed within
  1. 2.3%1 day
  2. 4.7%3 days
  3. 13.6%7 days
  4. 21.9%14 days
  5. 36.9%30 days
  6. 59.0%60 days
This job: posted 27 hours ago

When median: 12 days open

The posting

The Opportunity

Every year, tens of millions of Americans go through a coverage transition: a layoff, a resignation, a move into retirement, a 65th birthday while still working. It is one of the most consequential financial decisions a person makes, and it usually arrives as a twenty-page packet during the worst week of their professional life. Nobody owns it. COBRA makes the event compliant; it does not make it managed. That gap is expensive for employers and genuinely hard on people.

When is the enterprise platform for guided health insurance decisions at every qualifying life event. Through When Choice, When Medicare, and When ICHRA, we combine an intelligent decision-support experience with licensed, non-commissioned agents so every person understands their real options and lands somewhere good. We have supported more than one million employees and managed over 204,000 qualifying events for Fortune 50 and Fortune 500 employers, reducing COBRA enrollment by up to 80% while improving the experience for the people leaving. Doing right by employees and taking cost out are usually opposing forces. Here they are the same action.

Role Overview

We are hiring a Director, Member Services Operations: an operational expert who executes and scales member services through tools, data, and automation while delivering a superior member experience. You will lead the Member Services team: the licensed agents who guide members through coverage transitions, ICHRA enrollment, and Medicare decisions, along with specialists in enrollment, licensing, and other key roles as we grow.

This is a hands-on role on a team that runs today, and scale is the focus. You will manage quality and capacity, build the processes, tools, and automation that let the team handle more volume without losing quality, and use data to make decisions as volume grows.

How We Staff the Agency

When’s internal agent team is lean by design. We do not intend to build a large in-house contact center. A handful of full-time licensed agents carry our core member experience, set the quality bar, and handle our most complex situations. Everything above that baseline, including open enrollment peaks, large client launches, reductions in force, Medicare, and new ICHRA volume, is met through our agency and potentially via overflow agency partners and 1099 contract agents.

Capacity planning, partner management, and quality control across a blended workforce are therefore central to this role. Success is not measured by the size of the team you build. It is measured by whether members get excellent, compliant guidance regardless of who is on the other end of the call.

Responsibilities

Lead the existing team

- Manage When’s full-time licensed agents, including scheduling, coaching, and performance management.

- Own the member experience across phone, email, and chat, including outreach cadence, scripts, escalation paths, and enrollment workflows.

- Run quality assurance and training: call and email review, scorecards, calibration, and onboarding for every agent, internal or contracted.

- Serve as the escalation point on complex member situations, providing guidance and judgment rather than taking the queue.

- Lead and continuously improve the Member Services process across technical issues, platform troubleshooting, and non-technical member questions.

- Hire, onboard, and develop agents as the team grows.

- Build out the team as When scales, including specialist roles such as enrollment and licensing. You do not need to be licensed to manage them.

Tools, data, and automation

- Own the team’s tools and workflows in Zendesk, and work with Product and Technology on agent tooling, automation, and the digital-to-human handoff.

- Find opportunities to automate and simplify the team’s work, including with AI-assisted tools.

Capacity and contractor management

- Forecast capacity against open enrollment, Medicare AEP, January 1 ICHRA effective dates, client launches, and reduction-in-force events.

- Plan and manage capacity across full-time agents, partners, and contractors, and make the case for when to add each.

- Manage the 1099 contract agent network and overflow agency partners, including sourcing, training, ramp, seasonal activation, and performance review.

- Hold partner and contractor agents to the same quality and compliance standard as internal staff, with the monitoring to prove it.

- Own the budget for the team, including contractor and partner spend, and partner with leadership on the capacity and cost model.

Performance and reporting

- Own the agency KPI framework: speed to answer, abandonment, response time, first-contact resolution, quality, CSAT, productivity, enrollment completion, and COBRA participation rate.

- Turn performance data into operating decisions, and build the dashboards the team and leadership use.

- Supply Customer Success with member engagement and COBRA deflection data on a fixed cadence, and drive that measurement toward product instrumentation rather than manual compilation.

- Partner with leadership on how Member Services scales as volume and products grow.

Qualifications

Required

- 8+ years in customer support or contact center operations, including 4+ years leading teams.

- Strong technical skills: hands-on with Zendesk or a similar platform, workflow automation, and reporting tools, and comfortable using AI-assisted support tools.

- Highly analytical: comfortable defining KPIs, building dashboards, and turning performance data into operating decisions.

- Experience in health care, digital health, health insurance, benefits, or another health-related setting.

- Experience with capacity planning for volume that changes through the year.

- Experience managing outsourced, partner, or 1099 agent capacity alongside an internal team.

- Excellent communication, high emotional intelligence, and the ability to make complex health insurance topics simple.

- Effective in an early-stage environment: strategic when it matters, hands-on by default.

Strongly preferred

- Familiarity with HubSpot and business intelligence tools such as Metabase.

- Experience standing up a quality assurance program from scratch rather than inheriting one.

- Bachelor’s degree or equivalent relevant experience.

Reporting and Team

This position reports to When’s Co-Founder. You will lead the Member Services team and, as When grows and scales, build it out with roles such as an enrollment specialist, a licensing specialist, and other key roles. You will work closely with Customer Success, which owns the employer relationship. The Agency function owns the employee and member relationship, and the two work in close partnership.

Compensation, Location, and Travel

We offer a competitive salary ($150,000 to $170,000), we pay 100% of your health insurance, stock options and more. This role is remote, with minimal travel for company and occasional client meetings.

From $25, paid onceGet the CV for this job

What happens when you press

One press. We do the rest.

  1. A CV for this posting

    Written against When's own wording, from every piece of relevant proof in your profile.

  2. 25 readers review it

    Recruiter, hiring manager, skeptic and more read every draft, round after round. You get the best round.

    The review screen in CV Rocket: how each CV was read, round by round.

  3. We apply on When's form

    Our application engine gets through the hardest forms there are. Where a question needs you, AI suggests the best answer. Don't want us applying from our IP addresses? Use our Chrome extension: we apply straight from your own browser.

    An application in CV Rocket: every answer filled in on the employer's form.

  4. Every reply, sorted

    When's answer lands in your private mailbox, and we classify it on arrival: interview, question, rejection.

    The CV Rocket inbox: each employer reply classified as an interview, an action or a rejection.

  5. Reply with AI

    AI helps you write the email, checks it and sends it. We show you whether the recruiter read it.

  6. The interview in your calendar

    Full integration with your calendar. The invitation goes straight in.

    An interview invitation in the CV Rocket inbox, added to the candidate's calendar.
Get the CV for this job

From $25 per CV, paid once. No subscription.

Why it works

3×

more interviews than doing it yourself with ChatGPT.

ChatGPT writes a CV and never learns what happened to it. We see every reply. For each CV we know:

  • How it was written, and how the review scored it
  • When we applied, and how long after the posting went up
  • Which posting, which company, which city
  • Who got the interview, and who heard nothing

That is how we know which CVs get called.

Get the CV for this job

From $25 per CV, paid once. No subscription.

The numbers game

More applications. More interviews.

Every application goes out with its own CV, written for that posting and paid once. Send enough of them and the law of large numbers finds you the job.

Get the CV for this job
By hand5–10
With CV Rocket100
applications a day

Nearby

Live postings like this one

Same employer first, then the same role elsewhere.

Before you press

Straight answers

Get the CV for this job

From $25 per CV, paid once. No subscription.

What if my background isn't good enough?

We make the most of the background you have. The CV uses every piece of relevant proof your profile holds, and one of the 25 readers reads your whole profile and flags what the CV left out.

Do you really apply for me?

Yes, on the employer's own form, the hardest ones included. Where a question needs you, you answer it right there and AI suggests the best answer. Don't want us applying from our IP addresses? Use our Chrome extension: we apply straight from your own browser.

Is it a subscription?

No. You pay once per CV, from $25. Every application goes out with its own CV, written for that posting.

One job. One CV.
Paid once.

Pick the posting you want. We write for it, apply for you and catch the reply.

Get the CV for this job

From $25 per CV, paid once. No subscription.