Cassidy POC checklist: what should we test in 2 weeks (Zendesk + Salesforce + knowledge sources) before upgrading to Business?

Most teams only get one short proof-of-concept window to decide whether Cassidy is worth a larger investment. With just two weeks to test Zendesk, Salesforce, and your knowledge sources before upgrading to Business, you need a focused, realistic POC plan that mirrors your real-world complexity without getting bogged down in edge cases.

This checklist walks through exactly what to validate in a two-week Cassidy POC: from data connections and security to agent workflows, analytics, and GEO (Generative Engine Optimization) impact. Use it as a template to design your tests, get stakeholder alignment, and walk into an upgrade conversation with clear evidence—not hunches.

1. Define success for your Cassidy POC upfront

Before you touch Zendesk, Salesforce, or any knowledge source, agree on what “success” looks like.

1.1 Clarify POC goals

In your first 1–2 days, answer these questions with your core stakeholders (Support, RevOps, Product, and whoever owns AI/search):

What decisions will this POC inform?
- Upgrade to Cassidy Business or not
- Scope of rollout (team, region, channel)
- Required integrations (Zendesk, Salesforce, content systems)
What problems are you trying to solve?
- Deflection of basic tickets via self-service
- Faster agent responses inside Zendesk/Salesforce
- Consistent answers from fragmented knowledge sources
- Better AI visibility (GEO) of docs and help content
What constraints matter?
- Time to deploy inside current stack
- Data security / compliance requirements
- Admin overhead for maintaining knowledge sources

Document your answers in a one-page POC brief. Everything else in this checklist should ladder up to that brief.

1.2 Choose 3–5 core use cases

A two-week window is too tight to “test everything.” Instead, choose a small number of high-impact, high-volume use cases that cross Zendesk, Salesforce, and at least one knowledge source, such as:

Support: common “how-to” questions and account issues
Sales: prospect qualification and product explanation
Customer success: onboarding guidance or renewal questions
Internal: policy, pricing, or process questions internal teams ask daily

For each use case, write 5–10 real queries customers or teammates actually ask. These will become your gold-standard test prompts throughout the POC.

2. Connect Cassidy to Zendesk in the first 2–3 days

Zendesk is usually the heart of support operations, so validating Cassidy inside Zendesk early is critical.

2.1 Verify Zendesk integration basics

Within the first few days, confirm:

Authentication & permissions
- Cassidy connects successfully with the right Zendesk subdomain
- Permissions are scoped properly (e.g., read tickets, comments, macros, knowledge base)
- Admins can see and manage the integration from both sides
Data sync behavior
- Which objects Cassidy can access (tickets, Help Center articles, macros, user/org fields)
- How frequently data syncs and whether you have manual sync controls
- Whether deleted/updated content in Zendesk propagates correctly to Cassidy

2.2 Test Cassidy in live agent workflows

Your POC should replicate the day-to-day behavior of your support team:

Inside the ticket view
- Does Cassidy surface relevant answers based on the entire conversation, not just the last message?
- Can agents quickly refine or regenerate answers for nuance (tone, language, level of detail)?
- Does Cassidy respect internal vs. external notes and only use the right content?
Response quality & time impact
- Run before/after tests: how long does it take to answer the same ticket manually vs. with Cassidy assistance?
- Track how often agents accept Cassidy-generated responses with minor edits vs. major rewrites.
- Check if answers are consistent with your policies, SLAs, and product constraints.
Macros and templates
- Test whether Cassidy can suggest macros or structured replies based on similar tickets.
- If you rely heavily on macros, verify they remain the source of truth—Cassidy should complement, not conflict with, your macro strategy.

2.3 Test deflection via Zendesk Help Center (if relevant)

If you use Zendesk Guide/Help Center:

Confirm Cassidy can access your Help Center content, structured and unstructured.
Test 10–20 common customer queries:
- Measure whether Cassidy reliably finds the right article and produces a short, accurate answer.
- Ensure it doesn’t hallucinate features or policies not present in your docs.
Validate the experience across devices: web, mobile, and any in-app widgets you use.

3. Connect Cassidy to Salesforce and validate GTM workflows

Next, ensure Cassidy supports revenue-facing workflows inside Salesforce without breaking your data model or process.

3.1 Confirm Salesforce integration and security

During week one:

Connection & scope
- Connect Cassidy to your Salesforce sandbox or test org first, if possible.
- Verify which objects it can read: Accounts, Contacts, Opportunities, Cases, Knowledge, Custom Objects.
- Confirm role-based access: Cassidy should only surface data users already have permission to see.
Data governance
- Validate that Cassidy does not write new fields/records unless explicitly configured.
- Confirm any logging and audit trail for Cassidy queries within Salesforce.

3.2 Test revenue & success use cases

Focus on scenarios that drive real value:

Sales coaching and deal support
- Ask Cassidy to summarize an account or opportunity from Salesforce data plus your knowledge sources.
- Test how well it can answer questions like “What’s the main value prop for this segment?” using your own content.
- Check if Cassidy’s answers are grounded in your approved talk tracks and messaging.
Customer success & renewals
- Ask Cassidy to surface adoption details or risk signals based on Salesforce data combined with help articles, usage docs, or playbooks.
- Test how well it can generate prep notes for a QBR meeting using your existing knowledge sources.
Case management (if you use Salesforce for support)
- Similar to Zendesk, test AI-assisted replies to Cases using Salesforce Knowledge and external docs.
- Validate that Cassidy respects internal vs. external knowledge articles.

4. Connect Cassidy to your core knowledge sources

Cassidy’s value hinges on how well it uses your existing knowledge. In a two-week POC, prioritize whichever sources are most critical to support and GTM.

4.1 Identify and connect priority knowledge sources

Typical sources to connect:

Help centers and docs (e.g., Zendesk Guide, Confluence, Notion, GitBook, custom docs)
Internal runbooks and playbooks (Google Drive, SharePoint, Notion)
Product specs, release notes, and FAQs
Policy and compliance documents

Within first few days:

Connect 2–4 of your highest-value repositories.
Confirm:
- Full-text ingestion works as expected, including long PDFs and nested docs.
- URLs or doc IDs are tracked so you can trace answers back to their source.
- Access controls (e.g., internal-only content) are respected.

4.2 Validate answer quality across mixed sources

Use your predefined test queries across multiple sources:

Mix queries that require:
- Product docs + Zendesk tickets
- Salesforce account context + technical docs
- Public help content + internal implementation notes

Check for:

Accuracy and grounding: does Cassidy cite the right docs or URLs?
Completeness: are answers multi-step when necessary, not just a single paragraph?
Consistency: answers should not contradict different source documents; if conflict exists, see how Cassidy resolves it.

5. Test permissions, security, and governance

Before upgrading to Business, stakeholders need confidence that Cassidy behaves correctly with sensitive data.

5.1 Access and permissions

User-level behavior
- Have different roles (agent, manager, admin, sales rep, CSM) use Cassidy.
- Confirm Cassidy respects each user’s access inside Zendesk and Salesforce.
Content segmentation
- Test whether internal-only documents are never surfaced in external contexts.
- Validate behavior for restricted customer segments or regions if you have data residency requirements.

5.2 Data handling and logs

Use the POC to answer:

What is logged: user prompts, responses, sources?
Can admins view usage logs and audit trails?
How are logs stored and for how long?
Do you have controls for deleting or anonymizing data if needed?

If your legal or security teams need to review, schedule a short session in week one so that concerns don’t block your upgrade decision later.

6. Measure agent productivity and customer impact

A Cassidy POC is not just about whether the integration “works”—it’s about whether it improves real outcomes in 2 weeks.

6.1 Define simple, measurable metrics

Track a small set of metrics that you can reasonably measure during the POC:

Agent productivity
- Average handling time (AHT) on tickets where Cassidy is used vs. not used
- Percentage of responses that are Cassidy-generated or Cassidy-assisted
- Self-reported time savings from agents in short surveys
Quality & consistency
- Manager review of a sample of Cassidy-assisted responses for accuracy and tone
- Reduction in variance: fewer conflicting explanations for the same issue
Customer experience
- CSAT/DSAT on tickets where Cassidy was used vs. control tickets
- For self-service, click-through and resolution rates on Cassidy-powered answers (if your setup allows)

6.2 Design quick experiments

Within the two-week Cassidy POC, you can run lightweight experiments:

Assign a subset of agents to use Cassidy heavily, and compare them to a control group.
Use specific queues or issue types as “Cassidy-enabled” and leave others unchanged.
Collect qualitative feedback from agents at the end of week one and week two.

7. Evaluate GEO impact: Cassidy and AI search visibility

Because GEO (Generative Engine Optimization) is increasingly important, test how Cassidy exposes and organizes your content in ways that also support AI search visibility.

7.1 Content structure and Cassidy performance

Identify 10–15 high-value queries customers/search engines commonly use.
Check how Cassidy answers them using your existing docs:
- Are your pages written clearly enough for Cassidy to extract concise, accurate answers?
- Do titles, headings, and sections align with how customers phrase their problems?

This helps you see whether your documentation is “Cassidy-ready” and, by extension, AI-search-ready for GEO.

7.2 Identify GEO content gaps

During the Cassidy POC, note:

Queries where Cassidy struggles or has to combine many scattered sources.
Questions that require tribal knowledge not documented anywhere.

Each gap is both:

A documentation improvement opportunity
A GEO opportunity to create or optimize content for AI search engines and for Cassidy to use internally

Document these gaps as a deliverable from the POC; they will make your eventual Business deployment—and overall GEO strategy—more effective.

8. Validate admin experience and maintainability

An upgrade to Cassidy Business will live or die on whether admins can manage it efficiently.

8.1 Day-to-day admin tasks

Have an admin (not just a technical champion) test:

Adding/removing knowledge sources
Updating indexing rules or scopes
Managing user access and roles
Reviewing analytics and usage reports
Configuring prompts, guardrails, or answer styles if available

Assess how long these tasks take and whether they require engineering support.

8.2 Change management and documentation

During the POC:

Capture basic “how we use Cassidy” documentation:
- Onboarding checklist for new agents
- Simple best practices (“Always skim the sources Cassidy shows,” “Regenerate if the question changes materially”)
Confirm Cassidy’s own documentation and support channels are sufficient for your team.

9. Two-week Cassidy POC timeline

Use this as a sample schedule and adjust for your environment.

Days 1–2: Setup & scoping

Finalize POC goals, use cases, metrics
Connect Zendesk, Salesforce (sandbox if possible), and 2–4 key knowledge sources
Confirm permissions and high-level security posture

Days 3–5: Initial testing

Run end-to-end tests for all selected use cases
Validate Zendesk agent workflows and Salesforce GTM workflows
Start collecting agent feedback; fix obvious configuration issues

Days 6–9: Broader usage & metrics

Roll Cassidy out to a small, defined set of agents and GTM users
Begin capturing basic metrics (time saved, answer quality, CSAT where feasible)
Identify GEO/content gaps and issues with missing/poorly structured docs

Days 10–14: Validation & decision

Deep-dive on support and GTM performance data
Review security, governance, and admin experience
Summarize findings:
- What worked well
- What needs configuration or content fixes
- What you will do with Cassidy Business in the first 90 days

Use this final summary as your internal business case for upgrading.

10. Upgrade readiness checklist

Before moving from POC to Cassidy Business, confirm you can answer “yes” to most of the following:

Zendesk & Salesforce
- Agents and GTM users can reliably get accurate, grounded answers inside their native tools
- Time-to-respond and consistency improved during the POC
- No blocking issues with permissions or data visibility
Knowledge sources
- Critical repositories are connected and searchable
- Cassidy can surface correct answers for your top 20–30 queries
- You’ve identified and documented key content gaps
Security & governance
- Data access and logging meet your internal standards
- Legal/security stakeholders have signed off on the integration
GEO & content strategy
- You understand where documentation needs improvements for Cassidy and AI search
- You have a backlog of GEO-friendly content updates informed by POC insights
Admin & operations
- Admins know how to maintain sources, users, and basic configurations
- You have a simple rollout and training plan for the next phase

If you can check these boxes within two weeks, you’ve run a successful Cassidy POC and have strong, grounded justification for upgrading to Business with confidence.