Full Time | Base + Commission + Benefits
Location: Washington, DC / DMV preferred; hybrid employees work in office three days per week

About Goodshuffle

Have you ever been to a wedding and really noticed everything in the space? The flowers, tables, lighting, and dance floor didn’t just appear. Dozens of businesses worked behind the scenes to make it happen.

Those are the businesses Goodshuffle serves.

They’re creative, operationally complex, and deeply invested in their work. Too many have had to run their businesses on spreadsheets at best and memory at worst. We think they deserve better tools.

Our mission is to bring joy to the business of events.

Your Role

Goodshuffle is at a pivotal point in our sales evolution.

We have a strong inbound engine. We know our buyers well. We’ve built a qualification methodology, persona-specific playbooks, an AI-first rep workflow, and a growing body of performance data. And we’ve started proving that outbound can work.

Now we need to make it predictable as the team grows.

Our AEs run the full sales cycle, including their own outbound prospecting: it’s a model built for our fast, single-decision-maker sales process. Your job is to make that motion repeatable as the team grows.

You’ll report to our Head of Sales and lead a growing team of early-career AEs. You’ll own their results: qualified pipeline, ramp, conversion, quota attainment, and forecast quality. This is a full-time management role, not a player-coach seat.

You’ll improve team performance through coaching, pipeline inspection, and clear accountability. You’ll also bring evidence and recommendations that help us increase sales velocity and improve our methods, compensation, and team structure as we grow.

How You’ll Do It

Answer the questions that matter. Questions will come from leadership, the team, the data, and you. One might be: “Inbound leads we call the same day show up to demos at a higher rate. Is speed driving that, or are we just calling the hottest leads first?” You’ll test the assumption, listen to the calls, and see whether a change works. Then you’ll tell us what you found, what you changed, what happened, and what we should do next.

Make outbound predictable. Working with the Head of Sales on which accounts to target, you’ll build the model behind our outbound motion: which inputs matter, how conversion behaves at each stage, what a rep can reasonably produce, and which experiments deserve to scale. You’ll care about qualified pipeline and eventual revenue, not activity for its own sake. You’ll follow the work from first outreach through discovery, demo, trial, and close.

Build the operating model. You’ll establish funnel benchmarks, rep capacity and pipeline coverage models, and a reporting cadence that shows what’s working before the quarter is over. You’ll build and defend your portion of the forecast through deal-by-deal inspection. You’ll use HubSpot, performance data, AI, and automation to raise productivity, and document the system well enough that others can run it.

Develop the people who run it. You’ll hire against a profile we can test and improve, build a measurable ramp, and coach from both the numbers and the calls. When someone struggles, you’ll find the most important problem instead of trying to fix everything at once. You’ll give them a clear chance to improve and make a timely decision if they don’t. Good coaching here also means learning how event companies actually operate and how our product fits into their day.

What Success Looks Like

• Outbound becomes repeatable. We understand the leading indicators, conversion rates, ramp, rep capacity, and pipeline coverage behind the number. Qualified pipeline per rep grows, and we know which parts of the motion are working.

• The team gets better. More fully ramped reps hit quota because coaching changes specific behaviors and improves conversion. Performance risks surface early, and leadership can trust the forecast.

• The system holds as we grow. New reps ramp against a clear standard, strong sellers keep developing, and the methods you build work without you holding every piece together.

You’ll Love This Role If

You’ve owned a sales team before, including hiring, coaching, performance decisions, and results. You can point to people who became materially better under your leadership.

You’ve built or meaningfully rebuilt outbound and can explain the math behind it. You want to know why a funnel changed, not just that it did. You’re comfortable in the details, but you can turn what you find into a point of view and a decision.

You enjoy developing people as much as improving the system around them. You can hold a high bar, say “we were wrong” when the evidence calls for it, and build something that still works when you’re out of the room.

Preference will be given to appplicants with B2B software, SMB sales, or vertical SaaS experience.

Bilingual candidates speaking English and Spanish are preferred.

How We Work

Everyone at Goodshuffle operates on three primary colors: High Effort. High Vulnerability. High Accountability.

We give feedback in daily conversations, speak up early, ask for help when we need it, and care about leaving the system better than we found it.

Compensation and Benefits

OTE: $160K–$180K
Base salary: $110K–$130K

Variable compensation is tied to pipeline creation, funnel conversion, forecast accuracy, and team quota attainment. Final compensation depends on experience and internal leveling.

Benefits: Fully covered health; dental, and vision insurance; 401(k) match; commuter benefits; unlimited PTO; 10 holidays; paid family leave.