Pain points, rework, manual processes, and errors identified during the CKO Workshop (Feb 12, 2026), from recruiting process documentation, and from the Payroll Review Meeting (Mar 4, 2026). Grouped by process area.
Slack as WorkflowApprovals, change requests, and cross-team coordination all routed through Slack rather than structured systems
5
Manual System SyncGreenhouse/Workday mismatches, manual field checks, one-way integrations requiring human reconciliation
4
Edge Case GapsContractor conversions, upleveling, VIP onboarding, and working students lack defined processes
3
EMEA Manual BurdenBenefits administration, compliance windows, and right-to-work documentation disproportionately manual for EMEA
1. Hire to First Paycheck
23 flags
Recruiting
Create Job Requisition
Rework: If level needs adjustment, HM works with FP&A and budget owner - all coordination via Slack.
Recruiting Notes
Heavy Slack dependency for awareness and approvals instead of structured system workflows.
CKO Workshop
Review by Comp, FP&A, ELT
If manager decides to change anything after kickoff (up-leveling), this is a manual change requiring FP&A sign-off with recurring meetings and Slack.
CKO Workshop
Interface 1: Workday to Greenhouse
Changes to req title, level, and HM between role creation in GH and posting may cause inconsistencies if not caught by recruiter.
Recruiting Notes
If change happens in Greenhouse, the update to Workday is manual. Usually communicated via Slack.
CKO Workshop
Manual review does not check every field - checks job title but not job level.
CKO Workshop
Recruiter Screen
Right to Work: Only verbal confirmation obtained during recruiting. No formal document (Visa, Residence Permit, Citizenship) collected.
CKO Workshop
Interview Process
Legal check handled manually via email to Will Simmons - no structured/embedded workflow.
CKO Workshop
Check for skill overlap done with Comp team over Slack.
CKO Workshop
Offer Approval
Upleveling requires manual business case, connecting with FP&A via Slack for HC and budget approval, then internal parity check with PBPs.
CKO Workshop
Mark Hired & Notify
Recruiter must flag candidate as hired for subsequent steps to kick off - some manual chasing by the team to get the checkbox checked.
CKO Workshop
People Ops
Create New Hire Profile
Integration breakdowns usually caused by text field mismatches between Greenhouse and Workday - things like zip codes having dashes.
CKO Workshop
Once in Workday, POps gets notification to start compensation process. Comp, stock, and CF email entered here.
CKO Workshop
Submit Profile & Trigger Email
Workday cannot be accessed prior to hire date. Dual authenticator does not work yet.
CKO Workshop
Communicating to other stakeholders about onboarding type (VIP, confidential) is a gap.
CKO Workshop
People Ops also checks for anyone being "slow" and manually reaches out. Payroll deadlines can be a problem.
CKO Workshop
IT Provisioning
Onboarding sheet only updated once a day. Activation takes about 3 days. Communication issue back to People Ops team.
CKO Workshop
Laptop standards by role (Mac vs Windows) not clearly defined or enforced. Comp would prefer Windows.
CKO Workshop
Contentful Email should be activated one week prior to start date; process needs IT review.
CKO Workshop
Contractor conversion is a separate issue not well handled.
CKO Workshop
Pending Report & Compliance
POps does bi-weekly audits for compliance on the tight EMEA window to get all hiring documentation in - dependent on the new employee to respond.
CKO Workshop
Workday only moves when everything is completed; then POps gets it all at once. They want it to happen sequentially.
CKO Workshop
Benefits
Interface 2: Benefits Vendors
EMEA benefits processing is a very manual load for the benefits administrator.
CKO Workshop
Forma integration from Workday should be immediate but is currently only once a week. Suggestion: Okta-Forma integration.
CKO Workshop
2. Compensation - Main Comp Cycle
0 flags
No flags identified in this process area.
3. People Ops Audits
1 flag
POps Audits (Global)
Stock Grants Review
Stock/equity process does not properly handle contractor conversions, interns, or working students.
CKO Workshop
4. PAFs - Annual Variable Compensation
0 flags
No flags identified in this process area.
5. US Payroll Processing
8 flags
Payroll Specialist
New Hire Completeness Checks
No official new hire process specific to payroll. Tax election checks are fragmented across multiple checklist items.
Payroll Review (Mar 4)
Many completeness checks are vestiges from pre-integration era when Workday-OSV sync was unreliable. IT General Controls now govern that integration, enabling more system reliance.
Payroll Review (Mar 4)
Check State Registrations
New state registrations can hold up entire payroll if not caught before processing. No proactive notification from People Ops to payroll.
Payroll Review (Mar 4)
Chase Hourly Time Approvals
Managers consistently miss time approval deadlines despite calendar reminders. Payroll specialist has to chase or approve on their behalf with manual notation.
Payroll Review (Mar 4)
Run Bonus Reports
Redundant reports: same process checked multiple ways on different checklist items. Different checklist step but basically the same process done earlier.
Payroll Review (Mar 4)
Build Reconciliation
Reconciliation is a heavy manual spreadsheet process comparing multiple Workday reports with pivot tables. Very labor-intensive.
Payroll Review (Mar 4)
Fund Schwab 401K
Off-cycle 401K timing mismatch: Schwab gets funded immediately on ad hoc payments but Workday records it in next pay period, creating reconciliation variances that must be manually tracked and excluded.
Payroll Review (Mar 4)
December integration failure with Schwab went undetected - the funding completeness check would not catch election-level mismatches between what employees elected and what was actually sent.
Payroll Review (Mar 4)
Payroll Manager
Approve Payroll
Approval evidence is a Slack screenshot attached to reconciliation spreadsheet - not a structured system workflow or audit trail.