Head of Sales Development



Sales & Business Development
United States · Remote
Posted on Sunday, November 12, 2023

About Gladly:

Gladly is the only customer service software built around people, not tickets. Gladly applies AI differently, to help brands deliver radically personal customer service at scale, enabling consumers to help themselves and turning customer service agents into heroes by making them more productive. Every conversation starts with a real-time understanding of the customer. With every channel built-in – voice, email, SMS, chat, social messaging, self-service – companies have one, lifelong conversation stream with their customers. The world’s most loved brands including Allbirds, Bombas, Crate & Barrel, Ulta Beauty, and Warby Parker leverage Gladly to build lifelong loyal customers.

Our team loves working at Gladly because of its people, continuous growth opportunities, all in commitment to DEIB, collaboration, and culture.

Gladly is looking for a world-class Head of Sales Development to help us take our sales dev team to the next level and make outbound-sourced revenue more predictable. As the Head of Sales Dev, you’ll be an integral part of the Go-To-Market (GTM) team working closely with Marketing and Sales leadership to introduce Gladly to the market and uncover new opportunities. You have a proven record of leading high performing teams and delivering pipeline and revenue results — because pipeline only matters if it turns into ARR. You will report directly to Gladly’s Chief Marketing Officer.

What You'll Do:

  • Pipeline and Revenue. Collaborating with Sales and Marketing leadership to develop and execute sales development strategies that generate qualified new business opportunities and drive predictable pipeline growth that turns into ARR.
  • Demand Capture and Creation. At Gladly, we care deeply about our customers and our community. Our Net Revenue Retention is off the charts. This means that our outbound motions are not just about capturing demand. Sometimes we reach out and a prospect isn’t ready. You’ll need to figure out, in partnership with Marketing leadership, how to create demand. What story, talk track, assets can we offer that grow our prospects from problem aware to solution aware to Gladly product aware?
  • Sales Velocity. Understand the mechanics of our Sales Velocity model to know what sources, what campaigns, what sequences convert for which personas and verticals, how big the opps are and where they come from, how well they convert and how fast they convert to closed won business.
  • ICP. Understand intimately our Ideal Customer Profile (ICP), their pain points and trigger events. Develop intuition, along with data-driven insights, for what activities drive the biggest most viable opportunities quickest.
  • Math. You’ll need to see the quantitative path from the addressable market (accounts and contacts in our database) to day-to-day activities of the sales dev team (sequences, social outreach, calls, etc) to first order outcomes (first meetings) to ultimate results (closed won revenue). And you’ll need to find the best ways to optimize that path repeatably.
  • ABM. Partnering with the inbound marketing team on account-based marketing motions including strategic event attendance as a path to qualified pipeline.
  • Owning the number. Leading Gladly’s outbound pipeline generation team to deliver on new business revenue targets and other key KPIs, as identified.
  • People leadership. Recruiting, training, mentoring and developing our growing team of SDRs/BDRs, including one current team manager and two team leads, as well as designing career development plans.
  • Enablement. Training the team with a focus on skills development, pipeline management, and best practices.
  • Insights. Reporting on new business performance, and identifying trends and key learnings to improve future performance.
  • Growth Mindset. Establishing and continually refining new business processes, systems & tools to enable effective management of the pipeline and efficient collaboration with cross-discipline stakeholders


  • 7+ years of sales development leadership experience with a passion for building and leading high performing teams
  • Experience working in sales and marketing teams and collaborating deeply with both
  • T-shaped professional — you have specialized knowledge and skills in sales development, but also the desire, ability and proven experience in making connections across different disciplines
  • Intellectually curious especially about customers pains — you are deeply committed to understanding the business and challenges of Gladly’s prospects
  • Hustle and grit — you love winning and never give up
  • Strategic thinker with an analytical approach to problem solving — you love numbers and understand how they connect to the business
  • A results-driven mindset with a penchant for exceeding targets
  • Understanding of MEDDPICC sales methodologies
  • A champion for creativity and innovation, and for best-in-class customer experiences
  • Ability to attract, retain, and motivate a team of high performing BDRs; experience managing geographically dispersed teams is a plus
  • Excellent written/verbal communication skills
  • Experience working in an enterprise sales environment for B2B SaaS
  • Ability to drive cross functional alignment and collaboration across sales and marketing
  • Power user of Salesforce and other sales cadence and engagement software such as Gong, Outreach and other sales and marketing tools

Research has shown that individuals from marginalized groups are less likely to apply to jobs where they don't meet 100% of the criteria. Gladly values diversity of experience, so if you believe you have the right skill set, we welcome you to apply - even if you don't check every box in the job description. We're committed to an inclusive workplace and would love to see if you could be the next great addition to our team.


$230,000 to $255,000 per annum OTE (base + variable); equity, and benefits

For cash compensation, we set standard ranges for all U.S.-based roles based on function, level, and geographic location, benchmarked against similar stage growth companies. In order to be compliant with local legislation, as well as to provide greater transparency to candidates, we share salary ranges on all job postings regardless of desired hiring location. Final offer amounts are determined by multiple factors, including geographic location as well as candidate experience and expertise, and may vary from the amounts listed above.

Working at Gladly:

Putting people first is kind of our thing. Not only is it at the core of our product, but shapes our overall culture at Gladly—from our approach to hiring, to our benefits, and how we think about our place in the community.

We have embraced remote work and make it easy for our team to work from anywhere, but we also invest in opportunities to get the teams together in person regularly.

We have a strong work ethic, but value life outside of work, too.

Gladly Beliefs:

  • We win as one team: We believe the most important focus for us as a team is making the company successful.
  • We are successful when our customers succeed: We are committed to understanding the needs and expectations of our customers. We provide an exceptional product along with expertise and insight to help achieve their goals.
  • We believe in challenging the status quo: We know that our greatest strength is our ability to cultivate a growth mindset focused on reinventing customer service.
  • We value underdog grit: Success isn't always about having the most resources or the most experience; it's about having the determination and grit to keep pushing forward especially when it’s hard.
  • We strive to make every shot count: We will never have enough “shots on goal” so we strive to make every project, feature, customer presentation, the best it can be.
  • We embrace transparency: We know the best outcomes come from collaboration followed by communication of and commitment to the decision.

Our focus is on people and that starts with our employees. As an employee you can count on:

  • Competitive salaries, stock options
  • Medical, Dental, Vision and Life insurance
  • Generous paid time off
  • Generous paid Parental Leave
  • 401K
  • Flexible Spending Accounts
  • Home office stipends

Founded in 2014 by a team of repeat entrepreneurs with multiple successful exits, Gladly is reinventing customer service. By focusing on customers instead of tickets, we are disrupting a $70B market and are proud to count Crate and Barrel, Warby Parker and many other innovative brands as customers. Gladly has raised over $110M from Greylock Partners, NEA, GGV Capital, Glynn Capital and JetBlue Tech Ventures.

Gladly has made the decision to become a fully distributed company, allowing employees to live anywhere in the United States, and candidates to come from nearly any geographical region. That said, we also highly value our collaborative and creative culture and commit to meeting in real life as a company at least once per quarter when it is safe to do so.