Senior Director, Pipeline Strategy

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Job Description:

  • Own pipeline generation targets and outcomes across all segments
  • Set strategic direction on market segments, intent signals, and system optimization tradeoffs
  • Run weekly performance reviews covering fit, persona alignment, cadences, and meeting efficacy
  • Partner with the Global VP of Sales Development to design and launch organization-wide SDR initiatives
  • Optimize inbound and intent systems, including chat strategy, lead routing, intent data, and automated cadences
  • Equip regional and segment leaders with enablement content and lead scoring models
  • Chair cross-functional governance to prioritize tests and eliminate low-ROI channels
  • Oversee AI tool training and calibration for manager and rep needs
  • Operationalize top SDR strategies into playbooks for Account Executives to self-source pipeline
  • Align with Revenue Operations, Demand Generation, Product Marketing, Enablement, Sales, and Marketing
  • Report to the VP, Global Sales Development

Requirements:

  • 15+ years leading Sales Development, Revenue Operations, or Pipeline Strategy in B2B SaaS or high-growth environments
  • Deep fluency with intent platforms (e.g., 6sense), SDR engagement technology (e.g., Salesloft), conversational AI/chat tools, and CRM architecture (Salesforce)
  • Track record of using data—including account tiering, persona fit, and engagement metrics—to make strategic pivots that grow pipeline output
  • Exceptional communication skills and ability to align SDR, Sales Leadership, and Marketing around shared goals
  • Eligible for remote work within the United States, in locations where Smartsheet has a legal entity

Benefits:

  • Employer subsidized medical/vision and dental coverage for full-time employees
  • 401k Match to help you save for your future (50% of your contribution up to the first 6% of your eligible pay)
  • Monthly stipend to support your work and productivity
  • Flexible Time Away Program, plus Sick Time Off
  • Smartsheet-sponsored life insurance, short-term, and long-term disability plans
  • 12 paid holidays per year
  • Up to 24 weeks of Parental Leave
  • Personal paid Volunteer Day
  • Opportunities for professional growth and development including access to Udemy online courses
  • Company Funded Perks, including a counseling membership, local retail discounts, and your own personal Smartsheet account
  • Teleworking options from any registered location in the U.S. (role specific)
  • Market competitive incentive opportunity
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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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