Senior / Staff Software Engineer Job at Oscar in San Francisco County

Senior Platform Engineer - CRM & Data Systems

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

About the Company

We are a fast-growing Series B+ technology holding company that acquires mission-critical software businesses and accelerates their growth through our in-house engineering and go-to-market resources. Founded by industry veterans with backgrounds at top-tier venture capital firms and leading technology companies, we've completed 20+ strategic acquisitions in less than a year since founding.

Backed by institutional investors and notable angels from successful tech companies, we have tens of millions in revenue, strong profitability, and are expanding rapidly across major North American tech hubs.

The Role

Own the architecture and delivery of our CRM and data-driven prospecting platform in a zero-to-one environment. You'll transform complex, ambiguous problems into robust systems, standards, and processes that enable BD, M&A, and portfolio teams to operate at higher velocity. This is an AI-first orchestration role where you'll connect people, data, and systems to automate high-impact workflows and surface critical insights at precisely the right moment.

What You'll Do

Build the Source of Truth

• Design a unified "system of record + insight" that powers right-time outreach to top prospects
• Model entities (accounts, people, firms, signals) with sophisticated 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 preparation, and intelligent follow-ups
• Implement RAG pipelines so teams access 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 continuously updated
• Establish pragmatic privacy, reliability, and change-management practices across the platform

Prototype Fast, Scale What Works

• Partner directly with BD and M&A leaders to identify high-friction workflows and define measurable outcomes
• Deliver MVP automations rapidly, instrument impact metrics, and productionize winning pilots
• Define scalable standards including runbooks, schemas, system contracts, and SLAs that work across the portfolio

Technology Stack

You'll work across Salesforce and net-new applications with significant input on our greenfield stack:

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.)
• Frameworks: LangChain, LlamaIndex
• Vector stores: Pinecone, Weaviate, pgvector
• RAG patterns, prompt engineering, guardrails, evaluation frameworks

Orchestration & Reliability: n8n workflow automation, Temporal/Airflow (as needed), OpenTelemetry, Datadog monitoring

We maintain a greenfield stack where you'll have meaningful input on the tools we choose to deliver business outcomes.

Requirements

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

Technical Expertise:

• Proven track record building data-driven systems and workflow automation
• Experience with AI/ML integration, particularly large language models and RAG architectures
• Strong background in API integrations, event-driven systems, and data pipeline management
• Experience with CRM platforms (especially Salesforce) and go-to-market tool ecosystems

Leadership & Collaboration:

• Ability to translate ambiguous business requirements into scalable technical solutions
• Strong partnership skills with cross-functional business stakeholders
• Track record of rapid prototyping and scaling successful innovations
• Experience establishing technical standards and best practices

Compensation & Benefits

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

Equity: Competitive equity package with significant upside potential (getting in before Series C offers substantial long-term value creation opportunity)

Benefits: Comprehensive benefits package including health, dental, and vision coverage

Growth Opportunity: Direct exposure to M&A activities and portfolio company operations

Work Arrangement

Hybrid Options: 3 days per week on-site in major tech hubs (Toronto, San Francisco, New York)

Remote Available: Full remote work available for candidates based elsewhere in Canada

Visa Requirements: Open to visa transfers; new visa sponsorship not currently available

The Opportunity

This role offers the unique opportunity to architect next-generation AI-powered business systems in a high-growth environment. You'll work with proven leadership while building scalable solutions that define how modern companies prospect, engage, and accelerate their growth through intelligent automation.

Join us in creating the future of data-driven business development and portfolio management.

Desired Skills and Experience

Senior Platform Engineer - CRM & Data Systems
Technology Company | Full-Time | Hybrid/Remote
About the Company
We are a fast-growing technology company focused on acquiring and scaling mission-critical software businesses. Our leadership team brings experience from top-tier venture capital firms and leading technology companies. We accelerate growth through our in-house engineering and go-to-market resources.
Backed by institutional investors and notable industry angels, we've completed numerous acquisitions since founding. With strong revenue growth and profitability, we're expanding rapidly across multiple locations.
The Role
Own the architecture and delivery of our CRM and data-driven prospecting platform in a zero-to-one environment. You'll turn complex business problems into scalable systems, standards, and processes that help business development, M&A, and portfolio teams operate more efficiently. This is an AI-first orchestration role where you'll connect people, data, and systems to automate high-impact workflows and surface critical insights at the right moment.
Key Responsibilities
Build the Source of Truth

Design and implement a unified "system of record + insight" that enables strategic outreach to key prospects
Model entities (accounts, people, firms, signals) with robust identity resolution and data quality controls
Deliver self-serve reporting and dashboards with clear SLAs and business definitions

Orchestrate AI-First Workflows

Automate multi-step go-to-market and business development processes across CRM, email, LinkedIn, and messaging platforms
Deploy LLM-powered agents for research, content summarization, due-diligence preparation, and automated follow-ups
Implement RAG (Retrieval-Augmented Generation) pipelines to surface relevant documents, notes, and signals contextually
Fine-tune prompts, implement guardrails, and build evaluation frameworks 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 ensure data remains enriched, clean, and continuously updated
Establish comprehensive privacy, reliability, and change-management practices

Prototype Fast, Scale What Works

Collaborate with business development and M&A leaders to identify high-friction workflows and define measurable outcomes
Rapidly deliver MVP automations, measure impact, and productionize successful pilots
Define scalable standards including runbooks, data schemas, system contracts, and SLAs

Technology Stack
You'll work across established platforms and greenfield applications:
GTM Tools: LinkedIn automation, email platforms, Slack integrations, Clay
Development: Python, TypeScript (Node.js, React), GraphQL/REST APIs
Data Infrastructure: Supabase/PostgreSQL, event streaming, webhooks, identity resolution systems
AI/ML Platform:

LLM APIs (OpenAI, Anthropic Claude, etc.)
Frameworks: LangChain, LlamaIndex
Vector databases: Pinecone, Weaviate, pgvector
RAG architectures, prompt engineering, evaluation harnesses

Orchestration: n8n workflow automation, Temporal/Airflow (as needed), OpenTelemetry, Datadog monitoring
We maintain a modern, flexible stack where you'll have significant input on technology choices that drive business outcomes.
Requirements
Experience: 4-10 years in software engineering with meaningful ownership of CRM-centric platforms and/or revenue operations systems
Technical Skills:

Strong background building data-driven systems and workflow automation
Experience integrating AI/ML capabilities, particularly large language models
Proven track record architecting RAG systems and prompt engineering
Expertise in API integrations and event-driven architectures

Leadership Qualities:

Ability to transform ambiguous business requirements into scalable technical solutions
Strong collaboration skills with cross-functional business stakeholders
Experience prototyping quickly and scaling

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