Procurement & RFP Checklist for Buying Executive Assistant-a

Introduction

This guide provides a comprehensive, procurement-ready checklist and RFP framework to help large enterprises evaluate, select, contract, and manage Executive Assistant-as-a-Service (EAaaS) providers. It is written for procurement leaders, sourcing managers, legal counsel, HR partners, and business executives tasked with buying managed assistant services at scale.

Why buy Executive Assistant-as-a-Service?

EAaaS provides scalable, professional executive support delivered by trained assistants and managed through a vendor platform or service model. Enterprises buy EAaaS to:

• Rapidly scale executive support without hiring full-time headcount
• Standardize processes and quality across geographies
• Leverage vendor-managed training, technology, and redundancy
• Improve cost predictability via subscription or managed service pricing

What enterprise buyers should expect

Buyers should expect documented processes, clear KPIs, strong data protection, and the ability to integrate vendor operations with enterprise IT and HR policies. The procurement effort must align business stakeholders (executives, HR, legal, security) before issuing the RFP.

Procurement & RFP Checklist — Main Checklist

Use the following checklist as a template to structure requirements, evaluation, and contracting. Organize the RFP and evaluation into discrete sections so responses are comparable.

1. Requirements definition (Scope & Persona)

1. Define job personas: executive level (C-level, VP), required skills (calendar management, travel planning, project coordination), language capabilities, and time-zone coverage.
2. Specify service hours and coverage (core hours, on-call, 24/7 availability where applicable).
3. Document workload estimates: average hours/week, peak volume, and routine tasks vs. ad hoc duties.
4. Identify technology integration needs: calendar systems (Outlook/Google), CRM, expense platforms, vendor platforms, Single Sign-On (SSO) requirements.

2. Service delivery model

• Delivery type: Dedicated assistants vs. pool/shared model vs. hybrid.
• Snapshot of staffing model: hiring, training, retention, and backup/coverage procedures.
• Quality assurance: audits, peer reviews, supervisor oversight, and continuous improvement processes.
• Technology stack: vendor platform features, automation, collaboration tools, escalation workflows.

3. Service Levels and KPIs

1. Define measurable SLAs: response time, calendar changes processed, travel booking accuracy, expense processing time.
2. Agree on KPIs: first-contact resolution, customer satisfaction (CSAT), retention of assigned assistants, adherence to executive preferences.
3. Reporting cadence: weekly operational dashboards, monthly executive summaries, quarterly business reviews.
4. Remediation and credits: define penalties, service credits, and escalation paths for SLA breaches.

4. Security, compliance & data protection

• Data handling: data classification, storage locations, encryption at rest and in transit.
• Access control: least privilege, SSO, MFA, role-based access, logging of access to executive calendars, email, and other sensitive data.
• Background checks and vetting: criminal checks, reference checks, right-to-work verification.
• Compliance requirements: GDPR, CCPA, sector-specific rules (finance, healthcare), and cross-border data transfer mechanisms.
• Incident response: breach notification timelines, responsibility matrix, and tabletop testing frequency.

5. Pricing & commercial terms

1. Pricing models: per assistant FTE equivalent, pooled hours, subscription tiers, or outcome-based pricing.
2. Volume discounts and price escalation clauses: indexation, CPI, or agreed periodic review.
3. Included vs. billable services: onboarding, training, technology integration, travel bookings, out-of-scope requests.
4. Termination rights: notice periods, transition assistance, data return or deletion obligations, and migration support.

6. Implementation, transition & change management

• Onboarding plan: timelines, milestones, stakeholder responsibilities, pilot scope.
• Training program: vendor training, shadowing, knowledge capture of executive preferences and playbooks.
• Change management: communication plan, adoption metrics, and executive readiness checks.
• Exit and continuity: continuity plan, transfer of knowledge, and temporary support during transition to a new vendor.

7. Legal & regulatory considerations

• Contractual responsibilities: scope, warranties, indemnities, intellectual property, and confidentiality clauses.
• Labor law implications: contractor vs. employee classification, payroll obligations, and benefit impacts.
• Audit rights and compliance attestations: SOC 2, ISO 27001, or equivalent certifications where relevant.

Vendor Evaluation Scorecard

Design a weighted scorecard to compare vendor responses uniformly. Typical categories and recommended weights (adjust by enterprise priorities):

1. Service fit & capability — 25%
2. Security & compliance — 20%
3. Pricing & commercial terms — 15%
4. Implementation & transition plan — 10%
5. Operational excellence & KPIs — 15%
6. References & proof points — 10%
7. Innovation & roadmap — 5%

Scorecard design tips

• Use numerical scoring (1-5 or 1-10) and multiply by weight to derive a composite score.
• Require vendors to submit references and case studies with measurable outcomes.
• Run scripted reference checks asking the same questions across references.

Contract Negotiation Tips

Negotiation should align legal, procurement, and business stakeholders. Key negotiation levers include:

Typical negotiation levers

• Service levels and penalties: tighten SLA definitions, set realistic KPIs, and define clear remediation.
• Data protection assurances: insist on SOC 2 / ISO 27001 certification or contractually binding security measures.
• Termination and transition assistance: require vendor-funded migration assistance and knowledge transfer time.
• Price floors and caps: limit price increases and add volume discount floors to protect against usage fluctuations.
• Liability caps and indemnities: balance vendor accountability with realistic liabilities.

Contextual Background: Enterprise procurement considerations

Large enterprises face unique challenges when procuring services that interact directly with leadership and sensitive information:

• Stakeholder alignment is critical — executive preferences and HR policies must be captured early.
• Global footprint requires localized compliance approaches and data residency controls.
• Scale and continuity — enterprises require redundancy, succession planning, and 24/7 operational resilience where global leaders operate across time zones.

Procurement should map the buying process to enterprise sourcing governance: RFI & discovery, RFP issuance, vendor demos, proof-of-concept or pilot, final negotiations, and pilot-to-production transition.

Key Takeaways

• Define clear assistant personas and expected workloads before issuing the RFP.
• Prioritize security, compliance, and access controls equal to service capability.
• Use a weighted vendor scorecard to compare proposals and reduce subjectivity.
• Negotiate strong SLAs, transition assistance, and data return/deletion terms.
• Plan a pilot to validate operational fit and integration before wide rollout.

Frequently Asked Questions

1. What should be included in the EAaaS RFP executive summary?

Include a concise description of the enterprise, scope of expected services, targeted executive personas, desired service model (dedicated vs. pooled), timeline for implementation, and key evaluation criteria. This sets clear expectations for vendors and filters out non-aligned providers early.

2. How do I evaluate data security when buying EAaaS?

Ask for specific attestations such as SOC 2 Type II or ISO 27001, detailed data flow diagrams, encryption standards, access control mechanisms, background check policies, and incident response procedures. Include security as a high-weighted category in your scorecard and require periodic audits.

3. Should I run a pilot before full procurement?

Yes. A pilot (4–12 weeks) validates fit, integration, and user satisfaction. Define measurable pilot objectives, SLAs, and success criteria in the RFP so both parties understand the path to a larger deployment.

4. What pricing model is best for large enterprises?

There is no one-size-fits-all model. Popular options include per-assistant FTE pricing for dedicated support, pooled-hours subscriptions for flexible demand, or outcome-based models for specific deliverables. Enterprises often negotiate hybrid models combining base subscription with variable usage components.

5. How do I ensure continuity if a vendor-assigned assistant leaves?

Require documented backup and escalation processes, transition playbooks, overlap onboarding for replacements, and service credits for prolonged unfilled assignments. The vendor should guarantee a reasonable ramp time and provide interim coverage during transitions.

6. What KPIs matter most for measuring EAaaS performance?

Key KPIs include response time, accuracy of calendar and travel arrangements, CSAT or NPS, task completion rates, assistant retention, and SLA compliance. Regular reporting should be defined in the contract and reviewed in monthly and quarterly sessions.

7. How should legal review labor classification risks?

Legal should evaluate whether assistants are employees or contractors under applicable local laws. Clarify vendor employment practices, indemnities for misclassification claims, and obligations if local rules change. In some jurisdictions, additional safeguards or contractual clauses may be required.

Sources: industry procurement studies and best practices, vendor security frameworks, and enterprise sourcing guidance [1][2].

[1] Internal procurement benchmarking and vendor scorecard outcomes from enterprise sourcing studies. [2] Security and compliance frameworks including SOC 2 and ISO 27001 guidance.