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Benefits Operations Specialist in Boston

8 active opportunities · Updated October 2026

Explore current benefits operations specialist jobs in Boston. Filter by work mode, employment type, experience, department, date posted and distance.

D
📍 Boston, Massachusetts, United States· Full-time
✓ High-confidence listingCompany trend -83.5%

From $65K/yr

Quick readStrong listing-quality and freshness signals

As an Account Executive (AE) on our Commercial Sales team, you will assist in Datadog’s overall business growth by strategically engaging and closing net-new customers across small to midsize markets. Sellers follow a well-defined methodology, collaborate with internal stakeholders, identify the customer's unique needs, and clearly convey the value of the Datadog product. AEs have the opportunity to grow their careers in Sales and continue contributing to Datadog team success. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You’ll Do: Focus on net-new logo acquisition via outbound activity Become a Datadog expert through continued product and sales trainings Manage the full sales cycle, including technical demonstrations and negotiation Collaborate with Sales Development Representatives to drive top of funnel activity Strategically prospect into Chief Technology Officers, Engineering/IT Leaders, and technical end-users Who You Are: Curious, driven, and motivated as a sales person Creative in how you map and break into accounts Able to learn from feedback and champion a growth mindset Comfortable operating in a highly technical, fast paced environment Experienced in carrying quota, with a proven track record of success Fluent in Portuguese Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you’re passionate about technology and want to grow your experience, we encourage you to apply. Benefits and Growth: High income earning opportunities based on self performance New hire stock equity (RSU) and employee stock purchase plan (ESPP) Continuous professional development, product training, and career pathing Sales training in MEDDIC and Command of the Message Intra-d

AIGoRustSEM
D
📍 Boston, Massachusetts, United States· Full-time
✓ High-confidence listingCompany trend -83.5%

From $65K/yr

Quick readStrong listing-quality and freshness signals

As an Account Executive (AE) on our Commercial Sales team, you will assist in Datadog’s overall business growth by strategically engaging and closing net-new customers across small to midsize markets. Sellers follow a well-defined methodology, collaborate with internal stakeholders, identify the customer's unique needs, and clearly convey the value of the Datadog product. AEs have the opportunity to grow their careers in Sales and continue contributing to Datadog team success. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You’ll Do: Focus on net-new logo acquisition via outbound activity Become a Datadog expert through continued product and sales trainings Manage the full sales cycle, including technical demonstrations and negotiation Collaborate with Sales Development Representatives to drive top of funnel activity Strategically prospect into Chief Technology Officers, Engineering/IT Leaders, and technical end-users Who You Are: Curious, driven, and motivated as a sales person Creative in how you map and break into accounts Able to learn from feedback and champion a growth mindset Comfortable operating in a highly technical, fast paced environment Experienced in carrying quota, with a proven track record of success Fluent in Spanish Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you’re passionate about technology and want to grow your experience, we encourage you to apply. Benefits and Growth: High income earning opportunities based on self performance New hire stock equity (RSU) and employee stock purchase plan (ESPP) Continuous professional development, product training, and career pathing Sales training in MEDDIC and Command of the Message&nb

D
📍 Boston, Massachusetts, United States· Full-time
✓ High-confidence listingCompany trend -83.5%

From $65K/yr

Quick readStrong listing-quality and freshness signals

As an Account Executive (AE) on our Commercial Sales team, you will assist in Datadog’s overall business growth by strategically engaging and closing net-new customers across small to midsize markets. Sellers follow a well-defined methodology, collaborate with internal stakeholders, identify the customer's unique needs, and clearly convey the value of the Datadog product. AEs have the opportunity to grow their careers in Sales and continue contributing to Datadog team success. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You’ll Do: Focus on net-new logo acquisition via outbound activity Become a Datadog expert through continued product and sales trainings Manage the full sales cycle, including technical demonstrations and negotiation Strategically prospect into Chief Technology Officers, Engineering/IT Leaders, and technical end-users Who You Are: Curious, driven, and motivated as a sales person Creative in how you map and break into accounts Able to learn from feedback and champion a growth mindset Comfortable operating in a highly technical, fast paced environment Experienced in carrying quota, with a proven track record of success Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you’re passionate about technology and want to grow your experience, we encourage you to apply. Benefits and Growth: High income earning opportunities based on self performance New hire stock equity (RSU) and employee stock purchase plan (ESPP) Continuous professional development, product training, and career pathing Sales training in MEDDIC and Command of the Message Intra-departmental mentor and buddy program for in-house networking An inclusive company culture, opportu

D
📍 Boston, Massachusetts, United States· Full-time
✓ High-confidence listingCompany trend -83.5%

From $100K/yr

Quick readStrong listing-quality and freshness signals

As a Manager, Commercial Sales, you will provide strategy, mentorship, and guidance for a team of Commercial Account Executives. This role impacts one of the largest lines of business in the company, ultimately bringing a proven product to a multi-billion dollar market. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You’ll Do: Motivate your team to exceed objectives Develop and maintain accurate team forecasts Hire, oversee, and train a team of Account Executives Drive lead generation, high activity standards, and pipeline management Facilitate the ramp up for all new team members, coaching them to success Monitor the sales funnel from prospect to close and create metrics to improve performance Who You Are: Experienced in hi-tech direct sales Familiar with SaaS/Cloud and Salesforce Able to accurately forecast team performance Passionate about coaching, mentorship, and team management Motivated by helping people grow with a desire to continue learning A self-starter who thrives in a high-growth, rapidly changing marketplace Proven in overseeing an outbound sales team in all areas of the sales cycle Fluency in Portuguese at a professional or business level is essential for this position Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you’re passionate about technology and want to grow your experience, we encourage you to apply. Benefits and Growth: High income earning opportunities based on performance Opportunity for Presidents Club New hire stock equity (RSU) and employee stock purchase plan (ESPP) Continuous professional development, product training, and career pathing Sales training in MEDDIC and Command of the Message Intra-departmental me

AIRustSalesforceSEM
D
📍 Boston, Massachusetts, United States· Full-time
✓ High-confidence listingCompany trend -83.5%

From $100K/yr

Quick readStrong listing-quality and freshness signals

As a Manager, Commercial Sales, you will provide strategy, mentorship, and guidance for a team of Commercial Account Executives. This role impacts one of the largest lines of business in the company, ultimately bringing a proven product to a multi-billion dollar market. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You’ll Do: Motivate your team to exceed objectives Develop and maintain accurate team forecasts Hire, oversee, and train a team of Account Executives Drive lead generation, high activity standards, and pipeline management Facilitate the ramp up for all new team members, coaching them to success Monitor the sales funnel from prospect to close and create metrics to improve performance Who You Are: Experienced in hi-tech direct sales Familiar with SaaS/Cloud and Salesforce Able to accurately forecast team performance Passionate about coaching, mentorship, and team management Motivated by helping people grow with a desire to continue learning A self-starter who thrives in a high-growth, rapidly changing marketplace Proven in overseeing an outbound sales team in all areas of the sales cycle Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you’re passionate about technology and want to grow your experience, we encourage you to apply. Benefits and Growth: High income earning opportunities based on performance Opportunity for Presidents Club New hire stock equity (RSU) and employee stock purchase plan (ESPP) Continuous professional development, product training, and career pathing Sales training in MEDDIC and Command of the Message Intra-departmental mentor and buddy program for in-house networking An inclusive company culture, opport

AIRustSalesforceSEM
D
📍 Boston, Massachusetts, United States
✓ Quality checkedCompany trend -83.5%

Sales Development Representative As a Sales Development Representative (SDR), you will prospect, qualify, and generate customer leads to assist in Datadog’s overall business growth segment. By partnering with internal stakeholders, you will help IT and Technology innovators across markets recognize Datadog’s impact in their digital transformation and migration to the cloud. SDRs have the opportunity to grow their careers in Sales and continue contributing to Datadog team success. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You’ll Do: Collaborate cross-functionally with various Datadog teams Drive initial prospect qualification and schedule discovery meetings Develop, present, and implement strategies for acquiring new business Conduct outbound outreach by cold calling and emailing prospective customers Learn to follow a well-defined methodology to help identify a customer's unique needs Who You Are: Motivated by a career in sales Someone with an innate curiosity to learn Have a desire to succeed alongside teammates Proven in your written and verbal communication Comfortable with being able to learn from rejection Fluency in Spanish at a professional or business level is essential for this position Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you’re passionate about technology and want to grow your experience, we encourage you to apply. Benefits and Growth: High income earning opportunities based on self performance New hire stock equity (RSU) and employee stock purchase plan (ESPP) Continuous professional development, product training, and career pathing Sales training in MEDDIC and Command of the Message Intra-departmental mentor a

D
📍 Boston, Massachusetts, United States· Full-time
✓ High-confidence listingCompany trend -83.5%

From $50K/yr

Quick readStrong listing-quality and freshness signals

As a Sales Development Representative (SDR), you will prospect, qualify, and generate customer leads to assist in Datadog’s overall business growth segment. By partnering with internal stakeholders, you will help IT and Technology innovators across markets recognize Datadog’s impact in their digital transformation and migration to the cloud. SDRs have the opportunity to grow their careers in Sales and continue contributing to Datadog team success. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You’ll Do: Collaborate cross-functionally with various Datadog teams Drive initial prospect qualification and schedule discovery meetings Develop, present, and implement strategies for acquiring new business Conduct outbound outreach by cold calling and emailing prospective customers Learn to follow a well-defined methodology to help identify a customer's unique needs Who You Are: Motivated by a career in sales Someone with an innate curiosity to learn Have a desire to succeed alongside teammates Proven in your written and verbal communication Comfortable with being able to learn from rejection Fluency in Portuguese at a professional or business level is essential for this position Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you’re passionate about technology and want to grow your experience, we encourage you to apply. Benefits and Growth: High income earning opportunities based on self performance New hire stock equity (RSU) and employee stock purchase plan (ESPP) Continuous professional development, product training, and career pathing Sales training in MEDDIC and Command of the Message Intra-departmental mentor and buddy program for in

GitAIRustSEM
D
📍 Boston, Massachusetts, United States· Full-time
✓ High-confidence listingCompany trend -83.5%

From $90K/yr

Quick readStrong listing-quality and freshness signals

Mid-Market Account Executive As an Account Executive on our Mid-Market Sales team, you will assist in Datadog’s overall business growth by strategically engaging and closing net-new customers across mid-to-large size organizations. Sellers follow a well-defined methodology, collaborate with internal stakeholders, identify the customer's unique needs, and clearly convey the value of the Datadog product. Mid-Market reps have the opportunity to grow their careers in Sales and continue contributing to Datadog team success. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You’ll Do: Focus entirely on net-new logo acquisition Convert inbound leads to closed opportunities Leverage tools such as Sales Navigator and DiscoverOrg Strategically prospect into Chief Technology Officers, Engineering/IT Leaders, and technical end users (SRE, DevOps, DevSecOps) Multi-thread into different departments of a complex organization Collaborate with Sales Development Representatives to drive top of funnel activity Manage the full sales cycle, including negotiations and on-site technical demonstrations Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you’re passionate about technology and want to grow your experience, we encourage you to apply. Who You Are: Experienced in hunting and closing net new logos Able to strategically map out and break into large scale organizations Curious, motivated, and driven as a sales person Bold on the phones and creative in your emails Able to sit up to 6 hours, traveling to and from client sites via auto, train, or air, up to 30% of the time Benefits and Growth: High income earning opportunities based on self performance Opportunity for Presidents C

AIGoRustDevOps
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