How One Woman Built Squarespace’s Customer Care Team – From 1 to 184

Begin with a scalable onboarding plan and a transparent recruitment funnel to grow from 1 to 184. Check progress weekly, let autumnal priorities guide your campaigns, and scratch beneath the surface to identify what requires attention. When you hear candid feedback, you can increase capacity without stupid bottlenecks, and the plan will keep work flowing well. Creative women, who learn fast, set the tempo and help teams hear customer needs instead of guessing. Avoid cheat shortcuts by using guardrails, and rely on facts and a strong plan to stop chaos and keep care consistent.

From 1 to 184 took a deliberate, phased ramp. In the first quarter, the team added 2 agents and built a shared knowledge base. By the second quarter, 12 more joined, with a dedicated supervisor; onboarding shortened from 28 days to 14 thanks to a 5-week structured program and a shadowing phase. By month 12, headcount reached 60; month 18 hit 110; and by month 24 the team stood at 184. CSAT climbed from 84% to 91%, and average handle time dropped 22%. First-contact resolution rose to 78%. These facts show the impact of disciplined hiring and a three-tier care workflow on customer outcomes, supported by the leadership of a single determined woman who learned to balance process and empathy. The gods of responsiveness kept customers informed and agents confident.

A three-tier care model keeps tickets moving: Tier 1 handles chat and email with a living knowledge base; Tier 2 escalates to product specialists; Tier 3 tackles complex issues. A intuitive ticketing workflow helps new hires reach productivity in under seven days. Campaigns to preempt recurring issues reduce repeats by roughly one third. Automations handle simple tasks, leaving humans for nuance. Recruitment uses structured interviews and real-ticket simulations to avoid stupid shortcuts and to keep the pool diverse and creative. The result is a team that can respond quickly and maintain customer trust.

To apply this blueprint at your company, follow these steps: plan a 90-day ramp with clear milestones; establish a weekly check cadence; run campaigns to address known issues; keep a flexible staffing model; track facts and adjust; prioritize hiring women leaders and diverse talent; if teams havent faced this scale before, lean on product and operations partnerships to align support with product development. With tight coaching cycles, the team keeps improving and maintains customer empathy during peak periods.

In practice, the result is a care organization that can increase coverage without sacrificing tone. The story demonstrates how listening, planning, and creative hiring–driven by a single determined leader–can transform a support function into a scalable, reliable engine. If you apply the same ideas–learn, hear from frontline staff, and focus on customer outcomes–you’ll see similar gains in your own environment.

Scaling the care team: concrete steps from hiring to performance and communication

Start with a staged hiring ramp: fill core front-line roles in 6 weeks, then add leads and a trainer to support quality and scale.

1. Hiring plan and evaluation: Define three care roles (agents, team leads, trainer). Create a 5-point rubric: accuracy, empathy, reliability, communication, and learning agility. Use a two-part assessment: a writing task and a live chat simulation. Apply filters to ensure diverse applicants; target California-based candidates and remote talent across time zones. Set a target of 4–6 hires per week during peak ramp, with a 2-week interview loop and a decision window under 5 days. Use emails to invite candidates and track status in a shared board. Keep candidates engaged with clear timelines and regular updates to avoid drop-off; ensure interviews meet individual needs and reflect the roles.
2. Onboarding and readiness: Run a 7– to 10-day bootcamp covering product basics, brand voice, and support tooling. Introduce a triptych of scenarios (billing, technical, policy) to practice written responses and live responses. Establish a border between written and spoken handling by defining channel-specific guidelines. Ensure each person completes a knowledge base teardown and passes a written and oral test before taking live tickets.
3. Performance framework and metrics: Define a 90-day readiness requirement for each tier. Track CSAT and CSAT trend, first contact resolution (FCR), average handling time (AHT), and email response time. Set target levels: CSAT ≥ 92%, FCR ≥ 65%, AHT under 6 minutes for chat, and email replies within 1 hour, with monthly SLA compliance ≥ 95%. Conduct monthly calibration to avoid vanity metrics and to align perception with reality.
4. Communication cadences and channels: Establish daily 15-minute standups, a weekly metrics review, and a biweekly care-review with product input. Use three channels: emails for formal updates, chat for quick triage, and a ticketing system for traceability. Publish a short weekly digest and a longer monthly report. Keep everyone informed with clear ownership and timelines.
5. Cross-functional and leadership alignment: Involve founders and senior care leaders, beyond the care team, in onboarding debriefs and quarterly reviews. Create a feedback loop with product and success teams to surface recurring issues and feature requests. Use a collection of FAQs built from real tickets to reduce back-and-forth and speed up responses.
6. Quality assurance and growth: Implement weekly QA sampling of conversations with a 4-question rubric: tone, accuracy, resolution, and follow-up quality. Create a growth plan for top performers, including mentorship, channel rotation, and a formal career ladder. Track churn risk and address burnout quickly; maintain a border between workload and development.
7. Engagement and inclusion: Focus on women and other underrepresented groups; meets talent where they are with targeted outreach and internal mobility options. Provide ongoing learning, 15-minute micro-modules, and regular recognition to keep teams engaged. Use a welcome goodie and starter guide to reinforce belonging.

After implementing these steps, measure progress every quarter by headcount, channel mix, time-to-fill, and customer sentiment. The result is a care team that handles tickets and contributes to product feedback, policy clarity, and trusted user relationships.

Define initial roles, responsibilities, and 90-day ramp for new agents

Recommendation: Define three core roles for new agents: Frontline Agent (primary contact for routine inquiries), Specialist (handles elevated issues), and Escalation Liaison (coordinates complex cases). Pair each with a 90-day ramp and a local mentor such as Parker. Build a reference guide that maps tasks, metrics, and turn-time expectations for every role, which aligns with our vision for fast, friendly support.

90-day ramp structure: Week 1–2 onboarding and product familiarity, tools access, and a limited set of ticket types. Week 3–4 practice triage, compose high-quality responses, follow the knowledge base, and receive rapid feedback. Week 5–8 handle escalations under supervision and contribute to the guide with clear play patterns. Week 9–12 operate independently, own recurring issues, and deliver a weekly learning snippet to users; complete a structured review with your manager. Use a daily microlearning ritual, a weekly review, and a monthly performance check to turn learning into action.

Performance targets: Establish full capability by day 90 with questions resolved quickly and limited need for escalation. Target first response times: high priority within 10 minutes, medium priority within 1 hour, low priority within 4 hours for new agents; reduce escalations to under 15% of tickets by week 8; maintain CSAT above 4.6 and average resolution time under 24 hours for standard issues. Track knowledge-base contributions and user-reported helpfulness to ensure continuous improvement.

Operational guide and culture: Provide a concise guide and quick-start pack, plus a living reference deck. Schedule regular 1:1s to discuss progress, questions, and personal growth. Build trust with users through transparent feedback loops and shared ownership of outcomes. Capture unusual cases in Parker’s local knowledge base and encourage peers to learn from them, avoiding vanity fixes and missteps.

Build a scalable hiring and onboarding pipeline to grow to 184 agents

Launch a straightforward 12-week hiring sprint with four cohorts totaling 184 agents and a focused 2-week onboarding bootcamp for each group. Define three lanes–chat, voice/email, and back-office tasks–and assign a dedicated owner for each lane to keep progress visible. Use a single pipeline with clear SLAs, so every step from sourcing to first-week review happens on time.

Build a bank of 200+ pre-screened candidates after sourcing from referrals, job boards, and internal marketers. Pair recruiters with marketers to craft outreach; their writing should highlight a real growth path for an employee and a clear ROI. Use standardized interview modules to boost the highest chance of a successful match, and maintain a trust-based candidate experience that makes everyone feel valued.

Define screening criteria with a non-negotiable set of metrics: quick typing test, problem-solving scenario, and chat-handling capacity. In the first 15 minutes, gauge attitude and calm under pressure to filter those who doesnt align with customer care standards. Automate shortlist triggers after successful screening to speed up progress.

Run culture-fit and role-specific tasks in two concise rounds, with a decision window of 48 hours after the final panel. Offer letters are sent within 48 hours of a successful panel. The highest chance of acceptance comes when pay, role clarity, and growth path are clear. Use a transparent invoice and payroll onboarding path so new hires join without friction. Create a 4-week onboarding path with weekly milestones and a mentor system. Trust stands like a king: clear expectations, fast feedback, and transparent decisions keep new hires confident.

During onboarding, run a longer, hands-on training block that blends product knowledge, process guidelines, and live chat practice. Build a 4-week ramp with weekly outcomes, short writing tasks to sharpen communication, and a housecivilized checklist for equipment, access, and policy reading. Track progress daily and escalate issues via urgent channels when blockers appear.

To keep momentum, host a weekly standup that acts as the single source of truth for hiring progress. Build a simple, friendly dashboard showing seats by lane, conversion rates between stages, and cost per hire. Make sure the team sees what they control next, which builds trust and reduces anxiety. Align with finance on the invoice flow so vendors are paid on time and bottlenecks vanish. When this flow is tight, you lift times and the employee experience.

Standardize onboarding with playbooks, coaching cycles, and feedback loops

Implement a 4-week onboarding playbook with a fixed coaching cadence and fast feedback loops. Begin with a plain, task-driven schedule that pairs new agents with a mentor, a sample customer case, and concrete success criteria. Each day lists a task, a micro-skill to practice, and one customer view to study.

Structure the playbook around three modules: product knowledge, conversational skills, and operational rituals. Include practical assets such as call scripts, email templates, and a gallery of photos and photographs to reinforce concepts. Those visuals help new hires translate theory into action and reduce errors when facing real customers. The playbook also defines clear completion criteria and a simple rubric the team can share publicly.

Coaching cycles: set a cadence of two 30-minute coaching sessions per week, plus one shadow ride-along per cohort. Implement a structured call review after each session with a short checklist: tone, pace, and problem framing. Use phone-based practice for live calls and separate channels for emails and messages; track improvements in real time. A parker mentor can reduce ramp time and provide a friendly, conversational anchor for the first weeks.

Feedback loops: after each module, run a 15-minute feedback round with the agent and a supervisor. Collect metrics from the first 30 days: time-to-first-response, first-contact resolution, and CSAT. Use a simple feedback form and a quick thumbs-up/thumbs-down rating for each session. Compile a weekly report with those views to drive improvements in the playbook and coaching cycles.

Measurement and adjustment: monitor rates for escalations, average handle time, and customer satisfaction. If a learning gap appears, update the playbook within 48 hours and notify the team via brief emails, then implement the changes in the next cohort. Offer a small bonus for teams that hit targets consistently; it reinforces momentum and keeps agents engaged.

Operational tips: designate a door for onboarding to keep focus, and keep the space free of distractions. Use a plain, shared playbook that travels with every new hire, and a simple dashboard that shows progress through views and rates. Include roadside reminders–quick prompts that pop up during practice calls–to keep performance sharp. When the program lands, those improvements become obvious in customer cases and the overall support quality; the old approach is gone, and we move onward with confidence, often sharing photos and even naked honesty about what still needs work.

Set up operations: ticketing, routing, SLAs, escalation, and knowledge base

Implement a lightweight ticketing system backed by a clear routing map and defined SLAs to shorten response times and support scaling from the beginning. Built with a simple UI, the system looks intuitive to agents and remains responsive even on busy days.

The following routing rules drive efficiency: route by product area to specialists, apply time-zone aware handoffs, and set a standard escalation ladder. wherein tickets gain a first-assignment within 3 minutes for high priority, a 15-minute acknowledgment target, and 60 minutes before escalation to a supervisor. The system will proceed automatically, and they’ll receive clear communications in the ticket thread.

The knowledge base serves as a lifecivilized anchor for both customers and agents. It should be lightweight yet comprehensive, with snapshots of common issues, step-by-step routines, and search that returns results within seconds. Each article includes a brief raison for its approach, a display of related topics, and a history of updates. Governance ensures it stays current: weekly reviews by fernandez, syed, christa to confirm accuracy and customer-facing clarity. The knowledge base supports ubiquity of information across channels and reduces back-and-forth by offering self-serve options.

Operate with a clear goal and measurable cues: track first response time, escalation rate, and knowledge-base contributions. Use dashboards to display trends in the following areas: tickets opened per channel, average minutes to first contact, and rate of self-serve resolution. Set targets: a 15-minute first-acknowledgment for high-priority, 2 hours for medium, 8 hours for low, with 4-hour escalation windows. Review weekly to adjust routing and SLAs as needs shift.

In practice, the setup yields a sustainable, busy-but-controlled cadence. A helicopter view helps managers see bottlenecks, while snapshots at the supervisor level show queue health. The team built this process with a clear division of responsibilities and a bias toward fast, accurate replies. This lifecivilized culture centers on crisp communications, and the team proceeds with confidence, delivering consistent support even during peak hours.

Craft a subject line playbook: templates for common inquiries and actions

Recommendation: Keep subject lines under 60 characters, begin with the topic, then a clear verb, and add a specific detail to avoid ambiguity. Use action-oriented templates and personalize for context to convert open rates.

Templates: Products inquiries - Products: Availability check for [Product], Products: Quick question about features of [Product], Hello: Do you have [Product] in stock?

Templates: Orders and shipping - Shipping: Check status for order [#], Shipping: Expected delivery date for order [#], Billing: Invoice clarification for [Date]

Templates: Returns and exchanges - Returns: Request for return label for [Order], Exchanges: Size exchange for [Product] (order [#]), Refund: Status for [Order]

Templates: Account and access - Account: Password reset for [Email], Account: Unable to sign in after update, On behalf of [Department]: Access to [Tool] for [Name]

Templates: On behalf and collaboration - On behalf of [Name]: Help with [Topic], Together with [Team]: Request for a status update on [Project], Hello team: Please check [Link] and confirm

Templates: Exhibition and event inquiries - Exhibition: RSVP for Lake Photography Show, Photography: Request for prints and polaroids for triptych display, Exhibition: Collaboration on upcoming show

Templates: Links and resources - Links: Documentation for [Product], Links: Quick guide to [Topic] for [Team], Memory: Recap of our last chat and next steps, Receive: Confirmation of updated access

Tips for tone and optimization – Use customer-centric lines that mirror user goals; keep language concise and actionable; track metrics like open and click rates to tune templates; when a conversation looks tangled, offer a clear next step and a link to guidance; if a customer is pissed about a delay, acknowledge and propose a concrete remedy; for creative inquiries, weave imagery references like polaroids и triptych to signal relevance; limit emojis in subject lines to brand-aligned contexts; ensure subject lines reflect the actual topic to avoid confusion and boost memory recall; provide links to essential pages and maintain a calm, optimistic tone; if a customer requests updates, set expected receive times and honor them; think together with the user to reduce tangles and improve conversion, whether the inquiry is about exhibition logistics or photography products like a lake-view shot.