People & HR

How to manage benefits enrollment as Chief of Staff and Founder's Office

People & HRFor Chief of Staff and Founder's Office3 apps10 steps~20 min to set up

Benefits enrollment season hits a chief of staff like a second job that arrives on top of the actual job. You're the one chasing Paylocity or ADP reports to confirm who enrolled in what, cross-referencing against the headcount list you pulled from Google Sheets last week, and Slacking individual managers because three new hires from Q3 never completed their elections. HR owns the system; you own the coordination. That means you're the one building the enrollment status tracker in Notion, following up on the stragglers via Gmail, and then manually reconciling everything the night before the deadline. No one tool talks to the other, and you are personally the glue.

Build this on Starch → See the apps used

People & HRFor Chief of Staff and Founder's Office3 apps10 steps~20 min to set up

Outcome

What you'll set up

A live enrollment status dashboard that pulls headcount from Paylocity or ADP and flags every employee who hasn't completed their benefits election — no manual roster-building required.

An automated follow-up sequence that drafts and sends reminder emails to non-completers, routed through Gmail, so you stop being the human who copies the same 'please complete your enrollment' message twelve times.

A summary report you can drop into Slack or a Notion page for the CEO and CFO: total enrolled, pending, waived, and estimated monthly benefits cost impact — ready before the deadline, not the night of.

The Starch recipe

Apps, data, and prompts

The combination of Starch apps, the data sources they pull from, and the prompts you use to drive them.

Apps used

Scheduling Task Manager

Data sources & config

Starch syncs your Paylocity employee and benefits data on a schedule (payroll runs, employee records, time-off) and your ADP worker and org-unit data on a schedule. Gmail is synced directly so Starch can read enrollment-related threads and draft outbound reminders. Slack is connected so Starch can post daily status digests. Notion is synced so enrollment documentation and decisions live in a searchable knowledge base. Google Calendar is synced so deadline events block time and trigger automation runs automatically.

Prompts to copy

Build me a benefits enrollment tracker that pulls employee records from Paylocity, shows each person's enrollment status (complete, pending, waived), flags anyone overdue, and lets me filter by department and hire date.

Every morning during open enrollment, check Paylocity for employees still in pending status, draft a personalized reminder email for each one using Gmail, and send me a Slack message with the day's follow-up list before 9am.

Build me a task list for benefits enrollment close: deadline reminders for each carrier submission, owner assigned to each item, P1 flagged for anything due within 48 hours — and alert me via Slack if anything goes overdue.

Run these in Starch → or paste them into your favorite agent

Walkthrough

Step-by-step

1 Connect Paylocity (or ADP) — Starch syncs your employee roster, benefits elections, and enrollment statuses on a schedule. This becomes the single source of truth replacing the manually exported CSV you've been living in.

2 Tell Starch: 'Build me a benefits enrollment tracker showing every employee, their current election status, their department, their hire date, and a red flag if they're within 5 days of the deadline and still pending.' Starch builds the app; you don't write a single formula.

3 Connect Gmail — Starch syncs incoming messages so it can identify enrollment-related threads (carrier confirmations, employee questions, broker emails) and surface them without you digging through your inbox.

4 Set up the Email Triage app to route all benefits enrollment emails into a dedicated view: broker correspondence flagged high priority, employee 'how do I enroll?' questions drafted for reply, carrier confirmation receipts auto-filed.

5 Build the follow-up automation: 'Every weekday at 8am during the enrollment window, pull the list of employees still in pending status from Paylocity, draft a reminder email to each one using their name and manager, queue them for my review in Gmail, and post a summary to #hr-ops in Slack.'

6 Wire in Google Calendar — Starch reads your enrollment deadline events and triggers the automation sequence automatically, so you don't have to remember to run it manually on the right days.

7 Build the exception report: 'Show me any employee hired in the last 90 days who has not yet received a benefits introduction email, and draft that email using our standard onboarding language stored in Notion.' This closes the new-hire gap that always slips through.

8 Use the Task Manager app to track carrier submission deadlines — each carrier gets a P1 task with a due date, assigned owner, and a Slack alert if it hits overdue status. Tell Starch: 'Create tasks for each carrier submission deadline, mark anything due in the next 48 hours as P1, and ping me in Slack each morning with what's outstanding.'

9 Build the close summary report: 'Pull final enrollment counts from Paylocity broken down by plan type and department, calculate estimated monthly premium impact using the rate sheet I'll paste in, and format it as a two-page PDF summary I can send to the CFO.' Starch assembles the numbers; you review and send.

10 Publish a Notion page via the Knowledge Management app with the enrollment decisions, deadlines, carrier contacts, and this year's rate changes — so next year's chief of staff (or you, nine months from now) isn't starting from scratch again.

See this running on Starch

Connect your tools, describe what you want, and the agent builds it. Closed beta is free.

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Worked example

November 2025 Open Enrollment Close — 148 Employees

Sample numbers from a real run

Employees enrolled (medical)	131
Employees pending at day 8 of 10	17
Reminder emails drafted and queued by Starch	17
Employees who completed enrollment after reminder	14
Remaining manual escalations (manager call required)	3
Estimated monthly premium cost submitted to CFO	94,200

On day 8 of the 10-day enrollment window, Starch's 8am automation ran against the Paylocity sync and flagged 17 employees still in pending status — 9 in Engineering, 5 in Sales, 3 in G&A. Starch drafted a personalized reminder email for each, pulling their name, manager, and the specific plan deadline from Paylocity data. The chief of staff reviewed the queue in 6 minutes, made two edits, and sent all 17. By end of day, 14 had completed enrollment. The remaining 3 required a manager call — Starch flagged each as a P1 task with the employee name, manager, and a one-line context note. The close summary report — enrollment counts by department, plan type, and estimated $94,200 monthly premium impact — was assembled by Starch from the final Paylocity sync and dropped into the CFO's inbox before the 5pm board prep call. No pivot tables. No late night.

Measurement

How you'll know it's working

Enrollment completion rate by deadline (target: 100% of eligible employees)

Days from enrollment window open to full-roster confirmation

Number of manual escalations required (lower = better automation coverage)

Time from enrollment close to CFO cost summary delivery

New-hire benefits setup lag (days between start date and confirmed election)

Comparison

What this replaces

The other ways teams handle this today, and how the Starch version compares.

Paylocity / ADP native reporting

Gives you the data but no automation on top — you still manually export, filter, and chase stragglers yourself.

Notion + Google Sheets tracker (manual build)

Flexible but entirely manual; roster goes stale the moment someone is hired or termed and you forget to update it.

Rippling or Gusto benefits module

Handles enrollment within its own system well, but if your HRIS is Paylocity or ADP, you're adding another system rather than connecting the one you have.

BambooHR

Strong HR workflow tool, but the chief of staff still has to manually pull reports and build the cross-functional follow-up process outside of it — Starch connects to BambooHR from its integration catalog and wraps the automation layer on top.

On Starch RECOMMENDED

One platform — scheduling, founder inbox, task manager all running on connected data. Setup in plain English; numbers stay current via scheduled syncs and live agent queries.

Try it on Starch →

FAQ

Frequently asked questions

We use Paylocity for HRIS. Does Starch actually sync from it, or do I have to export CSVs?

Starch syncs your Paylocity data directly on a schedule — employees, payroll runs, benefits data, time off. No CSV exports. The enrollment tracker you build in Starch reads from that live sync, so when a new hire completes their election in Paylocity, it shows up in Starch automatically.

Can Starch actually send the reminder emails, or does it just draft them for me to send manually?

Both modes work. You can build the automation so Starch drafts emails into a review queue in Gmail (recommended if you want eyes on each one before it goes out) or you can tell it to send automatically after a review window. Gmail is a direct sync, so Starch reads and sends through your actual account.

What if our benefits broker uses a portal with no API — like a carrier website we log into manually?

Starch automates browser-based workflows through your browser — no API needed. If your carrier portal is a website you log into and click through, Starch can automate submission steps, scrape confirmation numbers, or check enrollment status pages. It's the same pattern as automating any other web-based tool.

Is this actually secure enough for employee benefits data?

Fair question to ask. Starch is not SOC 2 Type II certified today — that's worth knowing upfront. If your company requires SOC 2 Type II for any tool that touches HR data, that's a real constraint. Starch is honest about this: it's on the roadmap, not yet complete.

We have ADP, not Paylocity. Does that change anything?

No meaningful difference for this workflow. Starch syncs ADP worker records and org units on a schedule, the same way it syncs Paylocity. The enrollment tracker works the same way; you'd just connect ADP instead when you set up the data source.

Can I use Starch to track benefits enrollment across multiple legal entities or subsidiaries?

Yes. If your employees are distributed across org units in ADP or Paylocity, that structure comes through in the sync. You can tell Starch: 'Build the enrollment tracker segmented by org unit and flag any unit under 90% completion.' It builds the view from the synced data without you manually maintaining separate lists.

The task manager you mentioned for carrier deadlines — is that live today?

The Task Manager app is currently in development — you can request beta access. In the meantime, you can build a custom task-tracking surface in Starch by describing it: 'Build me a deadline tracker with carrier name, submission date, owner, and a Slack alert when anything goes overdue.' That custom app is available right now.