Director/Sr. Director, Commercial Operations

Opensend

2d•Remote

About The Position

At Opensend, we turn unknown website visitors into customers. Our platform reveals actionable identity insights, helping brands unlock first-party data, boost retargeting across channels, and increase customer lifetime value, without relying on form fills or purchases. Opensend is a 55-person, rapidly scaling, bootstrapped company with an enterprise B2B SaaS data platform gaining lots of VC interest. Weʼve grown 5x over the past year through great ideas, great people and hard work, and have acquired close to 1000 customers. As Director/Sr. Director of Commercial Operations, you will lead the strategy, systems, and processes that power Opensend’s go-to-market (GTM) engine serving ecommerce and DTC brands. This role is the head of commercial operations for the company, reporting into the COO, and integrates RevOps, Sales Operations, GTM Operations, and Pricing Operations into a unified function optimized for the needs of ecommerce merchants. You will serve as both architect and highly hands-on operator: designing frameworks, processes, and insights that unlock growth while personally driving the execution needed for scale in a lean, bootstrapped environment. You will partner closely with the leadership team, and Finance to support predictable growth, operational efficiency, and scalable revenue outcomes.

Requirements

8+ years in Commercial Operations, Revenue Operations, or Sales Operations roles in B2B SaaS, including ownership of significant cross-functional initiatives in high-growth environments.
Deep expertise across Sales Ops, RevOps, GTM Ops, and pricing/monetization, with a track record of building or materially upgrading these capabilities.
Experience supporting scale from roughly $10M ARR toward $100M+ ARR (or similar fast growth), ideally in a lean, bootstrapped or early-stage setting without a large VP layer.
Strong systems background: CRM (e.g., HubSpot or Salesforce), marketing automation, analytics, forecasting, enablement tools, and related integrations.
Strategic yet hands-on operator who can design frameworks and also directly execute, including building models, configuring systems, and driving projects to completion.
Exceptional analytical skills, with the ability to build financial and operational models, interpret data trends, and translate analytics into clear recommendations for the COO and GTM leaders.
Highly collaborative, effective at influencing without formal executive authority, and comfortable working with both executives and front-line GTM teams.

Nice To Haves

Familiarity with ecommerce, DTC, or retail ecosystems and related platforms (e.g., Shopify, Klaviyo or similar) is a strong plus.

Responsibilities

Lead the design and execution of the commercial operations blueprint that supports Opensend’s scaling from approximately $10M toward $100M+ ARR.
Partner with leadership on GTM planning and execution across targets, territories, capacity, coverage, and quotas.
Provide insights and modeling for annual/quarterly business planning, including seasonal revenue forecasting aligned with ecommerce peak periods (e.g., BFCM, holidays).
Establish and maintain a unified commercial metrics framework across pipeline, bookings, retention, and expansion, tailored to ecommerce merchant behavior patterns.
Develop merchant segmentation strategies (e.g., by GMV, platform, vertical, growth stage) and translate them into practical coverage and playbook recommendations.
Partner with Marketing leadership to refine multi-channel attribution models across paid social, email, SMS, and marketplace channels, and operationalize these models in reporting.
Architect and maintain territory design, lead routing, quota allocation, and compensation planning in close partnership with Sales leadership.
Build and continuously refine forecasting models, dashboards, and reporting that improve accuracy, accountability, and visibility for GTM leaders and the COO.
Use data-driven insights to help improve sales productivity, conversion rates, and deal velocity, and operationalize these improvements via process and system changes.
Optimize CRM configuration and processes, and drive the creation and maintenance of sales playbooks and enablement assets (onboarding guides, training content, competitive assets) in collaboration with Sales and Marketing.
Lead the design and optimization of the GTM tech stack (CRM, MAP, sales engagement, analytics, enablement, attribution tools) to support scale, efficiency, and actionable insights.
Ensure data integrity and a “single source of truth” across Marketing, Sales, and Customer Success by defining and enforcing core GTM data standards and metrics.
Implement scalable processes and automations across the customer lifecycle; from lead acquisition through renewal and expansion; that reduce manual work and errors.
Champion continuous improvement initiatives (workflow enhancements, tool integrations, process redesign) that reduce friction for GTM teams and improve time-to-insight.
Operate as a hands-on systems owner, capable of directly configuring tools and coordinating with vendors/partners where needed.
Partner with Product, Finance, and GTM teams regarding pricing and monetization operations and analytics by providing data-driven recommendations on pricing and packaging strategy.
Design and maintain pricing models and discount/approval frameworks that balance growth objectives with profitability, ensuring Sales has clear guardrails and flexibility where appropriate.
Conduct competitive pricing analysis, win/loss deal reviews, and collect customer feedback to inform pricing and packaging proposals to the executive team.
Support the development of packaging strategies for different customer segments (e.g., emerging brands vs. enterprise retailers) and coordinate cross-functional implementation once decisions are made.
Help maintain a lightweight governance process for pricing and packaging updates, ensuring changes are analyzed, documented, communicated, and rolled out smoothly.
Partner with Marketing to improve funnel efficiency, attribution accuracy, and the execution of campaigns that drive qualified pipeline.
Work with Customer Success to optimize expansion, renewal, and retention frameworks, using customer insights to inform GTM tactics and product prioritization.
Lead cross-functional GTM projects (e.g., new vertical plays, new market entries, platform integrations) as the operational owner and program manager, coordinating execution across teams.
Help define and operationalize merchant health scoring based on platform utilization, integration success, and business outcomes in collaboration with Product and Engineering.
Drive seasonal campaign and readiness planning aligned with the ecommerce calendar (e.g., Q4 prep, post-holiday optimization) across Sales, Marketing, and CS.
Serve as the operational backbone for commercial teams, leading through influence and cross-functional collaboration rather than direct executive authority.