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Oscar

Senior / Staff Software Engineer

Oscar, San Francisco, California, United States, 94199

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Overview Senior Platform Engineer - CRM & Data Systems at Technology Holding Company. This full-time, hybrid/remote role focuses on architecting and delivering a CRM and data-driven prospecting platform in a zero-to-one environment. The position emphasizes AI-first orchestration to connect people, data, and systems, automating high-impact workflows and surfacing critical insights at the right moment. Location options include San Francisco, CA; New York, NY; and Toronto, Canada.

Base pay range $200,000.00/yr - $250,000.00/yr

Technology Holding Company

| Full-Time | Hybrid/Remote | San Francisco, CA | New York, NY | Toronto, Canada

What You’ll Do

Build the Source of Truth

Design a unified system of record + insight to power right-time outreach to top prospects

Model entities (accounts, people, firms, signals) with identity resolution and data quality guardrails

Ship self-serve reporting and dashboards with clear SLAs and business definitions

Orchestrate AI-First Workflows

Automate multi-step GTM and BD processes across CRM, email, LinkedIn, and messaging platforms

Stand up LLM-powered agents for research, content summarization, due-diligence prep, and intelligent follow-ups

Implement RAG pipelines to surface the right documents, notes, and signals contextually

Fine-tune prompts, implement guardrails, and build evaluation harnesses for accuracy, tone, and safety

Integrate Data & Systems

Build and maintain bidirectional integrations between Salesforce and external data providers

Connect APIs, webhooks, and event streams to keep data enriched, clean, and up-to-date

Establish privacy, reliability, and change-management practices across the platform

Prototype Fast, Scale What Works

Partner with BD and M&A leaders to identify high-friction workflows and define measurable outcomes

Deliver MVP automations rapidly, measure impact, and productionize winning pilots

Define scalable standards including runbooks, schemas, system contracts, and SLAs

Technology Stack Work across Salesforce and greenfield applications with input on our stack, including:

GTM Workflows:

LinkedIn automation, email platforms, Slack integrations, Clay

Application Development:

Python, TypeScript (Node.js, React), GraphQL/REST APIs

Data Infrastructure:

Supabase/PostgreSQL, event streaming/webhooks, identity resolution systems

AI & Machine Learning:

LLM APIs (OpenAI, Anthropic Claude, etc.); LangChain, LlamaIndex; vector stores: Pinecone, Weaviate, pgvector; RAG patterns

Orchestration & Reliability:

n8n, Temporal/Airflow, OpenTelemetry, Datadog monitoring

We maintain a modern, flexible stack with meaningful input on tool selection to deliver business outcomes.

Requirements

Experience:

4-10 years in software engineering with ownership of CRM-centric platforms and/or revenue operations systems

Technical Skills:

Strong background building data-driven systems and workflow automation; AI/ML integration (LLMs, RAG); API integrations, event-driven architectures; CRM platforms (especially Salesforce) and GTM tool ecosystems

Leadership & Collaboration:

Ability to translate ambiguous business requirements into scalable technical solutions; strong cross-functional partnership; track record of rapid prototyping and scaling; experience establishing technical standards

Compensation & Benefits

Base Salary:

$200,000 - $250,000 USD (equivalent range in CAD for Canadian candidates)

Equity:

Competitive equity package with upside potential

Benefits:

Comprehensive health, dental, and vision coverage

Growth Opportunity:

Direct exposure to M&A activities and portfolio operations

Work Arrangement

Hybrid:

On-site 3 days/week in Toronto, San Francisco, or New York

Remote:

Full remote available for candidates based elsewhere in Canada

Visa:

Open to visa transfers; new visa sponsorship not currently available

The Opportunity: This role offers the chance to architect AI-powered business systems in a high-growth environment, working with leadership to build scalable solutions for modern prospecting, engagement, and portfolio management through intelligent automation.

Oscar Associates Limited (US) is acting as an Employment Agency in relation to this vacancy.

Note: This description reflects the responsibilities and qualifications of the role and is not an exhaustive list of duties.

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