Sell Checkout.comβs payments technology to mid-market and enterprise organizations, owning the sales cycle from prospecting and consultative payments strategy through negotiation, close, and account development.
GTM
π Description
- Own the self-serve-to-enterprise motion and create playbooks for selling, expanding, and telling Arcadeβs story.
- Run outbound and expansion experiments with Marketing and RevOps.
- Use product usage and revenue data to identify accounts ready for enterprise conversations.
- Coach customers on using Arcadeβs demos, video, and content to tell their product story.
- Lead enterprise pricing and packaging conversations for major opportunities.
- Share customer feedback with Product Managers.
π οΈ Requirements
- 3 to 5+ years in a customer-facing commercial role with closing or expansion experience. Traditional AE seats count. So do SE, CS, Account Management, PMM, agency, and founder-led sales, if you drove revenue.
- Experience at a fast-growing startup, ideally through an early-scale phase (10 to 100+ employees, $1M to $20M+ in ARR).
- Familiarity with product-led growth. You understand how self-serve users become enterprise buyers.
- A builder's instinct. You don't wait for a playbook. You write one, ship it, see what breaks, and iterate.
- Storytelling instincts. You can take a customer's messy goals and turn them into a clear narrative. Bonus if you've shipped something publicly that proves you can produce, not just pitch.
- Salesforce hygiene, clean pipeline, accurate forecasting.
- Data fluency. You use product signals and pipeline data to prioritize.
- Urgency, and the ability to collaborate across Sales, Marketing, and Product.
β¨ Benefits
- Competitive salary and meaningful equity
- Unlimited PTO and sick days
- 401k plus top-tier Health
- Dental
- Vision
- Remote work stipend and commuter benefits
- Meeting-light culture
- Biannual company retreats
- Notion, Linear, Superhuman
- A team that values diversity and inclusion
Full job description
The Role
Arcade is a creative tool. Our customers are marketers, sales leaders, PMMs, and product teams who want to tell a better story about their product. The person who helps them go from self-serve to enterprise needs to be part demo coach, part story strategist, part closer. They figure out what the customer is trying to say, show them how to use Arcade to say it, and close the expansion in the process.
You'll write the playbooks, run experiments, use product data to find the right accounts at the right moment, and ship the systems that turn this work from a craft into a repeatable motion. You won't just sell. You'll engineer how Arcade sells.
We're hiring for builders, storytellers, and former operators. If you've been an SE, PMM, agency strategist, growth marketer, founder, or a CSM who quietly drove a lot of expansion, keep reading.
What You'll Do
You'll own our self-serve to enterprise motion. Day to day, that means:
Write the playbooks for how we sell, expand, and tell Arcade's story as the team grows.
Run experiments with Marketing and RevOps to test new outbound and expansion plays.
Use product usage and revenue data to spot which accounts are ready for an enterprise conversation, and which still need time.
Work hands-on with customers to understand their use case and coach them on using Arcade's full product (demos, video, content) to tell their story.
Lead enterprise pricing and packaging conversations on our biggest opportunities, aligned to outcomes the customer already cares about.
Bring product feedback back to PMs who actually listen.
What We're Looking For
We care more about how you think than what's on your resume. That said:
3 to 5+ years in a customer-facing commercial role with closing or expansion experience. Traditional AE seats count. So do SE, CS, Account Management, PMM, agency, and founder-led sales, if you drove revenue.
Experience at a fast-growing startup, ideally through an early-scale phase (10 to 100+ employees, $1M to $20M+ in ARR).
Familiarity with product-led growth. You understand how self-serve users become enterprise buyers.
A builder's instinct. You don't wait for a playbook. You write one, ship it, see what breaks, and iterate.
Storytelling instincts. You can take a customer's messy goals and turn them into a clear narrative. Bonus if you've shipped something publicly that proves you can produce, not just pitch.
Salesforce hygiene, clean pipeline, accurate forecasting.
Data fluency. You use product signals and pipeline data to prioritize.
Urgency, and the ability to collaborate across Sales, Marketing, and Product.
How to Stand Out
Skip the cover letter. Send us a short Arcade you've built (real or fictional, pitch us anything) and a few sentences on how you'd spend your first 60 days. We read everything.
Benefits
Competitive salary and meaningful equity
Unlimited PTO and sick days
401k plus top-tier Health, Dental, Vision
Remote work stipend and commuter benefits
Meeting-light culture
Biannual company retreats
Notion, Linear, Superhuman
A team that values diversity and inclusion
Compensation
$220,000 to $260,000 OTE (50/50 commission), depending on experience and location, plus equity.
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