Jelena Ciaralli

Jelena Ciaralli

Strategic operations, scaled. AI in the mix. Honest before polished.

AI workflows in production Operating cadence design Founder partnership Process design from zero Partner launches end-to-end Portfolio health metrics
Case Studies

Strategic operations at Rayse

Aug 2024 – Apr 2026. First strategic operations hire at a Series A proptech.

Lean team. Growing pipeline of MLS partners rolling out the Rayse platform to their member real estate agents. No SOPs, no playbooks, no operating cadence. Four workstreams I scoped and shipped over 18 months.

Operating backbone

Mon/Wed/Fri cadence 3-tier escalation

Founders running on tribal knowledge and ad hoc execution. No system underneath.

  • Operating cadence. Mon/Wed/Fri rhythm with clear inputs and outputs per session.
  • 3-tier escalation framework so issues stopped landing on the CEO's desk by default.
  • Project archetyping so new work could be scoped against repeatable templates.
  • Notion portfolio with multi-views by partner, by stage, by owner.
  • Retro process that fed back into the templates each cycle.
Result. Issues routed and resolved without defaulting to the CEO. New work scoped against repeatable templates instead of starting from scratch each time.
Deep dive Walk through the full Ops Playbook

Repeatable launch system

12 MLS launches 2 masterclasses 40%+ registrant→attendee 60%+ attendee→login

Partner launches were happening but not predictably. I instrumented two conversion gates nobody was tracking: registrant-to-attendee on launch day, attendee-to-login on the platform after.

  • Comms sequence planned backward from launch day to build the funnel.
  • Cross-functional orchestration with each partner's marketing lead on announcement emails, audience lists, and reminder timing.
  • Standardized launch KPIs defined against the platform's existing reporting so every launch was measured the same way.
  • Post-meeting follow-up sequence to move attendees from interest to logged in.
  • Real-time quality signal. When numbers lagged, we could pinpoint why mid-launch (a partner who hadn't sent the announcement, a slipped reminder, a wrong audience list) and intervene before it compounded.
Result. Hit 40%+ registrant-to-attendee and 60%+ attendee-to-login targets across launches. 12 MLS launches end-to-end on a consistent timeline.

AI workflows

LLM workflows Human review

Team spending more time on admin than on partners. AI as leverage, not as replacement.

  • LLM workflows for partner reporting. Structured inputs, structured outputs, human review before send.
  • Stakeholder communication drafting with style controls so the voice stayed consistent.
  • Project tracking and meeting synthesis so the team spent more time on partners and less on admin.
Result. Recurring admin tasks pulled off the team's plate without losing quality control.

Vendor consolidation

~$50K/yr saved 2 → 1 MLS data aggregators

Paying two MLS data aggregators in parallel. No clean read on whether we needed both.

  • Feed-usage by brokerage pulled from both aggregators to see who was actually using which feed.
  • Cost-per-feed layered in so the spend tied back to actual coverage, not headline contract terms.
  • Quality analysis on feed completeness, refresh cadence, and field-level accuracy where the two vendors overlapped.
  • Consolidation plan ranked by partner coverage risk, walked through with the founder and integrations lead, then migration and contract termination executed.
Result. Cut from two aggregators to one with zero partner gaps. ~$50K/year out of the vendor stack and a cleaner integration footprint.

Internal tooling at Enspire for Enterprise

Mar 2020 – Mar 2022. Product Owner / Product Manager.
~$60K/yr saved ~$10K/mo new revenue 3 engineering teams

Problem. Internal tooling gaps across the org. Third-party CRM didn't fit the business. Reporting disconnected from the ad and call-tracking data the team used. SEO team's client work wasn't visible in any shared system.

What I built.

  • Proprietary CRM platform, replacing the third-party tool that didn't fit. Roadmap and backlog across three agile engineering teams.
  • Customer-facing dashboard for enterprise clients to track local-business performance across ad campaigns, marketing channels, and call-tracking data.
  • SEO team's reporting tool. One input from the team, three synchronized outputs: client report, internal dashboard, and live site update.
Results. ~$60K/year saved by replacing third-party tooling. ~$10K/month in new recurring revenue from integrated reporting.

Before that: a decade of teams and delivery

Mar 2013 – Feb 2020. Web.com, Jacksonville. Supervisor → Manager of Design Services → Implementation Manager.
60+ person global team 100+ locations onboarded in 6 months 90%+ CSAT, 3 years running

Seven years at Web.com before the startup chapter. Led a design services org of 60+ designers, supervisors, and managers across India, the Philippines, Canada, and the US. Three consecutive years above KPI: customer satisfaction over 90%, site turnaround under 2 days. Then moved to implementation, onboarding 100+ behavioral health and franchise locations in 6 months, talking to every client 4 to 5 times a week, meeting 95% of timeline commitments. The AI chapter came later. The people leadership started here.

AI Builds

Smaller AI workflows I've shipped outside the featured project. Each one trades a recurring manual task for a one-input trigger.

Notion · Markdown

Repeatable initiative generator

Markdown templates that turn a single end date into a fully scaffolded Notion project. Tasks, milestones, and owners spun up in one pass.

  • Input: end date + initiative type
  • Output: structured Notion project, ready to staff
  • For: ops teams that ship the same play on repeat
Reporting · Markdown

Monthly reports, filtered and shipped

Markdown-driven workflow that pulls monthly performance data, applies a per-client filter, and delivers the report straight to client inboxes.

  • Pulls source data on a schedule
  • Filters per-client config
  • Drafts and sends the polished report
How I work
Schema first.
Lock the inputs and outputs before the prompt. If the shape isn't clear, the workflow drifts.
Human-in-the-loop.
AI drafts, humans ship. Especially when the audience is a partner or senior leader.
Build for the next operator.
Write SOPs as if handing them to someone less experienced. That's the real test.
Cadence beats heroics.
A weekly rhythm with clear inputs catches more than ad hoc fire drills.
Usage data first.
Vendor and tooling decisions follow what people actually use, not what they remember using.
Skills
Strategic & Business Operations. Strategic planning, cross-functional initiatives, process design, project scoping, stakeholder management, vendor and contract strategy, operating cadence design.
AI + Automation. LLM workflow design, prompt + schema engineering, human-in-the-loop quality review, AI enablement and training.
Customer Experience + GTM. Customer onboarding, technical onboarding (SSO, API, data integrations), partner launches, adoption + engagement.
What people say
She steps into ambiguity and turns it into clear, scalable systems that actually move the business forward. The kind of person you can count on to dig in, ask the right questions, and figure it out when the path isn't obvious.
Yvonne J. Thomas
Rayse colleague
Real Estate Technology Leader · 25+ yrs brokerage & MLS partnerships
via LinkedIn →
She dissected complex tasks and transformed them into methodical, actionable steps. After our collaboration, I'm not only confident about our services, I'm excited for the growth opportunities, thanks to the foundation she laid.
Andrea Blake, CMP
Consulting client
Operations, Bambiz
Elder Law & Estate Planning Marketing
via LinkedIn →
She developed an innovative reporting system that was previously unheard of in our organization, presented in a clear, visually engaging way. She excels at organizing and leading cross-functional teams from inception to completion.
Kendall Barker
Enspire for Enterprise colleague
SEO Manager
Amplifyed
via LinkedIn →