Sales Development & Deal Operations Lead

About Quickplay

Quickplay is the Content to Value Operating System for media and entertainment, connecting every stage of the content lifecycle—from ingest and enrichment to publishing and monetization—through one orchestrated AI system. We power streaming for Tier-1 operators including Warner Bros. Discovery, TelevisaUnivision, Telekom Malaysia, Television New Zealand and Gray Media. 

Headquartered in Toronto with offices in Los Angeles, San Diego, Chennai, Quickplay is the proven foundation broadcasters, sports operators, streamers, and creators rely on to turn their catalog into revenue. 

About the Role

Quickplay is hiring a Sales Development & Deal Operations Lead to drive new capabilities and capacity within the CBO office.   This role is one of the most leveraged roles on our commercial team—someone who will operate at the intersection of sales, marketing, and business development. The role is intentionally split 50/50 between two halves: opening new opportunities at the top of the funnel and quarterbacking our highest-priority deals through to close.

This is also an AI-forward role. We expect this person to help us build out the agent stack that handles the operational layer of sales—CRM hygiene, pipeline reporting, board-deck generation, content drafting, and research—so that they, the sales team, and business development can spend their time on the work that actually moves deals: pitching, judgment calls, and relationships. If you're someone who sees AI as leverage rather than overhead and who wants a hand in shaping how a modern sales org operates, you'll have room to do that here.

What You'll Own

Top-of-Funnel Development (≈50%)

You'll build and run the outbound motion in close partnership with the sales and marketing teams. That means:

• Developing target account lists with a clear strategic thesis, working with leadership to refine ICP and identify the highest-value segments for this quarter.
• Designing and launching outbound sequences against those targets, collaborating with marketing on messaging and positioning.
• Personally delivering the five-minute Quickplay pitch on discovery calls to qualify opportunities and move prospects into the sales pipeline.
• Supporting marketing campaigns with insights from your outbound work—what resonates, which segments respond, what objections emerge.

The hunt is yours to run, but you're not alone: marketing provides the content engine, sales leadership sets the strategic direction, and AI agents handle list research and sequence drafting so you can focus on the pitch and the relationship.

Deal Quarterback for Priority Opportunities (≈50%)

For our highest-priority deals—the ones where multiple stakeholders, budgets, and timelines are at play—you'll act as the project manager alongside the sales executive. Your job:

• Own follow-ups and scheduling so deal momentum doesn't stall between customer calls.
• Orchestrate internal tasks: pricing approvals, technical scoping, timeline construction, proposal assembly.
• Coordinate with product, solutions engineering, and finance to make sure nothing falls between meetings.
• Manage deal hygiene in the CRM so leadership has real-time visibility into what's actually moving.

The sales executive focuses on selling and the customer relationship; you make sure the machine keeps running. This is the role that turns a 90-day cycle into a 60-day cycle.

Building the Agent Stack

Across both halves of the role, you'll help us identify, build, and operate AI agents that handle the operational layer:

• CRM hygiene and pipeline reporting: Agents enforce data standards, flag stalled deals, and generate weekly dashboards.
• Executive and investor decks: Agents pull pipeline data and produce first-draft board decks; you add narrative and strategic commentary.
• Target research and enrichment: Agents compile account research, funding data, news, and contact info; you apply judgment and prioritize.
• Sequence drafting and outreach: Agents draft sequences; you personalize and refine the high-value touches.
• Content production: Agents draft blog posts, social content, and campaign materials; you edit, refine, and ensure brand voice, coordinated with the CMO and external event advisors.
• Event logistics: Agents handle scheduling, calendar coordination, and follow-up sequencing, coordinated with the CMO and external event advisors.

You won't need to be an engineer—but you should be the kind of person who, when faced with a repetitive task, instinctively asks "could an agent do this?" and then goes and figures out how.

What We're Looking For

Experience: A few years working in a sales or sales operations role where you've both opened opportunities and helped run deals. That could mean SDR-into-AE, sales ops with deal-desk exposure, or a hybrid sales/marketing role at a startup. We care more about evidence you've done both halves than a specific title.

Comfort pitching live. This role talks to prospects, not just about them. You need to be comfortable delivering a five-minute pitch and handling objections on a discovery call.

CRM fluency. Working knowledge of HubSpot or a comparable platform. You should be comfortable with pipeline metrics, conversion analysis, and building dashboards. If you've set up automations or reporting workflows, even better.

Genuine AI fluency. You've used Claude, ChatGPT, or similar tools to rethink how you work. Ideally, you've configured agents, automations, or AI-assisted workflows and have specific examples of what you automated and what you got back as a result. You don't need to code, but you need to think like an operator who sees AI as a tool to multiply your leverage.

Strong written communication. You'll draft and edit outbound sequences, review AI-generated content, contribute to customer-facing materials, and help shape Quickplay's narrative in the market.

Comfort in ambiguity and startup environments. You're willing to build processes where none exist and thrive in fast-moving, cross-functional settings.
Willingness to work within Quickplay's brand language standards. The brand language bible is mandatory reading in week one.

What Sets a Strong Candidate Apart

• B2B SaaS or sports/media technology experience. Ideally, you've sold into sports leagues, teams, media companies, or telcos. If not, you have a genuine appetite to learn the space quickly.
• A track record of using AI to compress operational work, with specific examples. E.g., "I built a workflow that turns a 4-hour reporting task into 15 minutes of review" or "I configured a Slack bot that syncs deal data automatically so I don't have to update the CRM by hand."
• Exposure to complex enterprise deals where multiple internal functions (product, legal, finance, solutions engineering) had to be coordinated to reach a signature. You understand the politics and the timeline.
• Experience in a sales/marketing hybrid or sales ops role where you wore multiple hats and thrived in the ambiguity.

Why This Role Matters

Quickplay is at an inflection point. We're scaling our sales motion, and we need someone who can unlock leverage through AI and process while still maintaining the high-touch, high-judgment work that closes big deals. This role is the pivot point: you'll make the sales team 2-3x more effective not by grinding harder, but by being smarter about what humans should do versus what machines should do.