Revenue Operations Contractor

Overview The Carpool Group is a New York-based fashion partnerships agency that brokers and executes cross-industry collaborations between emerging fashion designers (such as Ian Charms and Jane Wade) and global brands (such as Red Bull, Pinterest, JanSport, Nike, etc). Our primary business development engine is outbound email. We run targeted cold and warm email campaigns on behalf of retained clients to a database of approximately 10,000 brand contacts. We are hiring a contractor for a focused engagement to audit our current tech stack and eliminate friction (or redundancy) between systems. This person is excited to build a fit-for-purpose foundation with a functional, automated outreach engine. The goal is not ongoing maintenance - it is to design and implement a clean system that our internal team can operate independently once the engagement ends. The Problem We Need Solved Currently our sales data lives across Lemlist (email campaigns), Pipedrive (CRM), RocketReach (contact sourcing), and Google Sheets with no reliable sync between them. This creates real operational risk: contacts get emailed twice, warm leads get cold-pitched, and the team has no single source of truth for outreach or engagement status. Specific failures we need to fix: No deduplication: contacts receive campaigns they should be excluded from (e.g., someone actively in conversation gets a cold intro email) Campaign reply data doesn't flow back to the CRM: there's no automated handoff from 'emailed' to 'in talks' No cross-client conflict check: the same brand contact can be pitched for two different designer clients simultaneously Campaign schedule and status only exist in manual notes, not in a trackable system No Slack or team notification when a prospect replies or a status changes Where the Opportunity Is Beyond fixing what's broken, a strong contractor will recognize that TCG's outreach infrastructure has meaningful untapped potential. The right system design could unlock the following down the line: Opportunities to build toward:  Predictive contact targeting: use historical conversion data to score and rank new prospects before outreach, so the team is always working the highest-probability contacts first  Social signals as intent data: surface brands that have recently engaged with a client's content as a trigger to prioritize or personalize outreach  Automated warm lead sequencing: contacts who previously expressed interest or took a call get enrolled in a separate re-engagement sequence automatically, with no manual effort from the team Self-updating contact database: the system flags job changes, stale records, and newly relevant brands rather than the team discovering them mid-campaign  Campaign intelligence layer: a running view of what subject lines, targeting criteria, and send patterns correlate with replies across all clients, so every new campaign builds on everything we've learned  Fully founder-independent operations: the team runs campaigns, manages replies, tracks deal progress, and reports to clients without the founder touching any of it The bigger picture:  Cold outreach is our current engine, but it's not the endgame. As we build stronger brand relationships, the measure of success shifts from volume of contacts reached to depth of relationships maintained. The highest-value outcome isn't a one-time deal, it's a brand partner who comes back season after season. In 6-12 months, we will have used the above-described system to build a rich network of relationships and context that supercharges our ability to service our clients.   We want a contractor who understands this trajectory. The system you build should make it easy to identify repeat partners, nurture long-term relationships proactively, and eventually replace cold prospecting with intelligent, relationship-first outreach: reaching fewer people, with more relevance, at exactly the right moment. Scope of Work Phase 1: Audit & Recommend (Week 1) Review current stack: Lemlist, Pipedrive, RocketReach, Google Sheets, Slack, Claude (Cowork) Meet with key Carpool Group team members individually to assess current process, needs, and gaps Identify where data breaks down and where manual effort is duplicating what automation could handle Recommend whether to keep Pipedrive or migrate to a more integrated tool (e.g., Apollo, which consolidates contact sourcing and CRM) Assess the need for a separate project management or account management system (or potentially leverage for ex for both CRM + PM)  Deliver a written system design doc outlining the recommended architecture before any build begins Phase 2: Build & Integrate (Weeks 2–4) Connect Lemlist campaign data to CRM with automated status updates Build deduplication logic: contacts marked as 'In Talks,' 'Partnered,' or 'Do Not Contact' are automatically excluded from new campaigns Set up cross-client conflict logic: flag if a contact is already being targeted for another designer client Create a master campaign tracker (Google Sheet or CRM view) showing: campaign name, sender, send date, volume, A/B test variant, and status Set up Slack notifications for key triggers: new reply received, contact status change, campaign launched Implement a follow-up cadence rule: exactly 1 follow-up at 7 days, stop after 2 total touches Phase 3: Handoff & Documentation (Weeks 5–6) Document all workflows with step-by-step SOPs the internal team can follow Train the existing team (2–3 people) on how to operate the new system Deliver a 'break-glass' guide: what to do if something breaks or gets out of sync 30-minute async handoff recording walkthrough What Success Looks Like One source of truth: contact status in the CRM matches Lemlist campaign data at all times Zero duplicate outreach incidents: the system prevents a contact from being emailed if they're already in an active conversation The internal team can run weekly campaigns without needing technical support A campaign performance report can be pulled in under 15 minutes by a non-technical team member The founder is not involved in any operational outreach decisions Current Tech Stack Lemlist (email campaigns), Pipedrive (CRM — underutilized), RocketReach (contact sourcing), Google Sheets (lead database ~10K contacts), Slack (new, early adoption), Claude Cowork. We are open to switching or consolidating tools — tool recommendations are part of the engagement. Ideal Background 3+ years in sales operations, revenue operations, or marketing automation Hands-on experience with Lemlist or similar cold email platforms (Instantly, Smartlead, etc.) Experience building CRM workflows: Pipedrive, Apollo, HubSpot, or equivalent Comfortable with no-code/low-code automation tools: Zapier, Make, or native integrations Experience incorporating AI tools and agents into workflows and enabling teams Has done this type of systems integration project from scratch before and can move fast Strong written/verbal documentation skills: the handoff is as important as the build How to Apply Send a brief note to with: (1) a description of a similar systems integration project you've completed, (2) the tools you used, (3) your resume/cv, and (4) your proposed rate and availability. We'll schedule a 30-minute intro call to walk through the current setup and answer questions. Shortlisted candidates will be asked to submit a high-level implementation proposal before any engagement begins