Sendblue is the leading iMessage-based business messaging platform, purpose-built for enterprise teams. We help revenue, ops, and customer success teams communicate through iMessage, which delivers significantly higher open and response rates than traditional SMS, while providing the native, trusted experience Apple users expect.
As an Enterprise Account Executive, you will own the full new business sales cycle for high-value enterprise accounts. This is a pure hunting role built for a closer who thrives on complex deals, multi-stakeholder navigation, and winning logos that matter. You will be the tip of the spear for Sendblue's enterprise go-to-market, targeting large organizations across verticals where real-time, high-deliverability messaging is mission-critical.
You will target organizations ranging from Series B+ tech companies to Fortune 1000 enterprises, with particular emphasis on Salesforce-native organizations where Sendblue's direct CRM integration provides immediate and measurable ROI.
Compensation & OTE
Commission: 10% of the first 12 months of total contract value for every deal closed
Sales Target: $2M – $5M in annual contracted revenue
OTE Range: $320,000 – $650,000 (uncapped)
Commission is earned on the full value of the first 12 months of each contract at signing, giving you maximum upside on multi-year deals closed early. There is no cap on commission earnings.
Culture Fit
- 1. Output Over Activity We’re not going to babysit how many emails you send. We measure how many logos you close. If you're the type that is obsessive over your own numbers before your manager asks, you'll be in good company.
- 2. Speed as a Competitive Advantage In enterprise sales, speed is a weapon. The rep who follows up faster, moves deals faster, and closes faster wins. We expect you to move like the deal is always about to go cold, because it is.
- 3. Pipeline Is Your Responsibility If your pipeline is thin, that's on you. Not marketing, not the product, not the economy. Relentless prospectors don't wait for permission, they build.
- 4. Every Day Is Day One You close a $500K deal on Friday. Monday, your pipeline is still your problem. There's no coasting here, only building toward the next one.
- 5. Urgency Without Chaos Relentless doesn't mean frantic. It means you wake up knowing your numbers, knowing your next five moves, and executing them without being asked. Calm, deliberate, relentless.
- 6. The Standard You Set Nobody here will push you harder than the market will. We look for people who've already internalized that, who don't need a quota to know what effort looks like.
- 7. Builders Only Sendblue is still writing the enterprise playbook. If you need the infrastructure built before you can perform, this isn't the moment for you. If you want to be the person who builds it, and wins while doing it, this is exactly the moment.
Your First 6-Weeks
Success at Sendblue Looks Like…
- 1. Flex Your Book & Call Your Shots By day 5, you’ve locked in your target accounts. You didn't wait for marketing to hand you a list. You already have meaningful relationships where you can get wins. You showed up with the accounts you want, segmented, and prioritized using criteria you know will move the needle.
- 2. Run the Full Demo Solo By day 10, you’re flying solo. You’ll have notes and support resources, though you won’t need them. You’ve internalized the product fast enough to pitch it confidently to a cold prospect. Speed of product mastery is a direct proxy for sales IQ.
- 3. Booked Calls By day 14, you’ve already had calls on the calendar and shown that you have the pull to get real stakeholders engaged. Not from an inbound lead. From your own network. This is the clearest early signal that you can generate pipeline independently.
- 4. Activate The Channel By day 21 you’ve already moved through the Salesforce Ecosystem leveraging partner angles to move the needle. You’ve aligned with a Salesforce AE, SE, or partner manager, and are actively getting involved in deals.
- 5. Has 2 Active Pilot Conversations By day 30, you’ve got real pilots in-late stage deal cycle. Not demos, actual pilot conversations where procurement, legal, or a VP is engaged. This means they moved fast enough and qualified hard enough to compress a cycle that most reps would drag out.
- 6. Closes or Advances the First Deal By day 45, a signed pilot, LOI, or a contract in legal. Not everyone will close in 6 weeks, but the right person will have something tangible in motion that leadership can point to.
- 7. Someone on the Team Says "I Want to Work With This Person" Intangible but real. You’ve shown up with energy, shared intel from calls, made others better in Slack or on a team call. A great enterprise AE makes the team smarter just by being in the room, and you’ll feel it immediately. Be that person.
What You’ll Do
New Business Development
- Own and execute the full enterprise sales cycle from outbound prospecting through contract close.
- Build and maintain a healthy pipeline at 3-4x quota coverage at all times.
- Target Salesforce-native enterprises (Sales Cloud, Service Cloud, Marketing Cloud) where Sendblue's native integration delivers immediate productivity gains.
- Run structured discovery and solution design sessions with VP- and C-level stakeholders.
- Structure commercial proposals, negotiate enterprise contracts, and drive deals to signature.
Executive Relationship Management
- Establish and maintain senior executive relationships within target accounts, including CROs, VPs of Sales, and COOs.
- Navigate complex buying committees with multiple stakeholders across revenue, IT, legal, and operations.
- Build relationships within the Salesforce partner ecosystem to source co-sell opportunities and accelerate deal velocity.
Strategic Positioning & Market Expansion
- Articulate Sendblue's value proposition against alternative messaging and outreach platforms.
- Represent Sendblue at Salesforce Dreamforce, industry conferences, and executive roundtables.
- Partner with Product and Marketing to deliver customer insights that sharpen the enterprise ICP.
- Identify expansion and upsell opportunities within accounts and hand off smoothly to Account Management post-close.
Cross-Functional Collaboration
- Work in close coordination with Sendblue's partnerships team, including aligned integration partners.
- Collaborate with Marketing on ABM campaigns targeting strategic enterprise accounts.
- Provide accurate and timely pipeline reporting within CRM.
Note: Travel extensively (up to 50%) to meet prospects on-site, attend industry conferences, and conduct executive briefings. This role requires a strong willingness to be on the road — building relationships face-to-face is a critical part of closing enterprise deals at this level.
Skills & Experience
Required
- 7+ years of enterprise B2B sales experience, with a demonstrated track record of closing deals in the $100K–$1M+ ACV range.
- Proven success as an enterprise hunter, net new logo acquisition is your primary competency.
- Experience selling into Salesforce-native organizations or within the Salesforce partner ecosystem.
- Ability to manage complex, multi-stakeholder deal cycles of 3-9 months from first contact to signed contract.
- Strong executive presence: you can run a boardroom conversation as confidently as a technical demo.
- Consultative, outcome-driven sales methodology (MEDDIC, Challenger, or equivalent).
- CRM proficiency (Close.com required); familiarity with sales engagement tooling.
Preferred
- Deep familiarity with the Salesforce AppExchange ecosystem and ISV/GSI partner dynamics.
- Experience selling communication infrastructure, messaging platforms, or SaaS productivity tools.
- Existing executive relationships at Salesforce-heavy mid-market and enterprise accounts.
- Background in outbound-led sales motions at a high-growth startup or scale-up.
- Entrepreneurial mindset, you're comfortable building playbooks in a fast-moving environment with limited hand-holding.
What You'll Be Selling
Sendblue enables enterprise teams to send and receive iMessages and SMS at scale through a platform that natively integrates with Salesforce, HubSpot, and other major CRMs. Unlike traditional SMS tools, Sendblue delivers:
- Significantly higher open and response rates than SMS, powered by iMessage infrastructure
- Native Salesforce integration, messages logged, triggered, and tracked inside the CRM
- Enterprise-grade compliance, security, and reporting
- Measurable impact on reply rates, pipeline velocity, and customer engagement
About Sendblue
Sendblue (Round One Inc.) is a fast-growing B2B SaaS company redefining how enterprise teams communicate. We're building the infrastructure layer for iMessage-powered business communication, a category we're creating, not competing in.
This is a high-visibility, high-upside role at a company with strong product-market fit, a lean and talented team, and the infrastructure to support a serious enterprise motion. If you want to own a market, not just work a territory, this is your seat.