Remote Lead Lead Junior Junior Remote Apprentice Programme Manager in Boston

At ClickUp, we're building the future of work: the first truly converged AI workspace unifying tasks, docs, chat, calendar, and enterprise search, all supercharged by context-driven AI. We are an AI-native company. Every team member is expected to leverage AI daily, and we evaluate AI fluency as part of our hiring process. Join us and help redefine what's possible. 🚀 What You’ll Own Lead, coach, and develop a team of Account Executives focused on the commercial segment across AMER. Drive pipeline generation, deal execution, and consistent attainment of regional revenue targets. Build a strong operating cadence around forecasting, pipeline inspection, deal reviews, rep development, and performance management. Hire, ramp, and retain high-performing talent while creating an ambitious, inclusive, and motivating team culture. Improve sales process scalability through better use of CRM data, performance metrics, and repeatable best practices. Partner closely with Growth, Marketing, Operations, and Product to improve conversion, support important accounts, and remove friction in the customer journey. Reinforce high standards for thoughtful, value-based selling and customer-first leadership. Report on performance, pipeline health, forecast accuracy, and improvement opportunities to senior leadership. Required Qualifications Significant experience leading B2B SaaS sales teams in a commercial, SMB, or mid-market motion. Strong understanding of selling across AMER markets and how regional nuance shapes coaching, hiring, and execution. Proven track record coaching high-performing sellers and improving team productivity, forecast quality, and revenue outcomes. Experience building or scaling repeatable new-business and outbound motions. Strong analytical and operational instincts, with comfort using CRM data, sales metrics, and pipeline insights to drive decisions. Excellent communication, collaboration, and change-management skills. Ability to influence partners across Marketin

For over 20 years, Smartsheet has empowered teams to manage work seamlessly and scale solutions smarter. Now, in our most ambitious chapter yet, we are uniting human teams with AI agents. By orchestrating the work agents do best, automating manual tasks and uncovering insights at scale, we create the space for people to focus on what truly matters: judgment, creativity, and big thinking. That is magic at work, and it’s what we show up for every day. Smartsheet is seeking change agents to join our Central/East Commercial Sales Team as an Account Executive . You will be responsible for increasing software sales and driving expansion across a territory of accounts. You will be motivated, passionate, and opportunistic. You will be a proactive and curious member of the commercial sales team, identifying growth opportunities for clients before they identify a need or gap for themselves. This remote role is part of the Commercial Sales team based in the US and reports a Manager, Commercial Sales. You Will: Build and manage a sales pipeline to meet or exceed software and services sales quotas within your book of business Execute a solution-based sales process encompassing multiple groups within our commercial mature accounts equivalent to (500-4,999 employee size) Develop new business opportunities within existing customers by analyzing and proactively targeting high-value needs across multiple departments and lines of business Leverage existing relationships to expand Smartsheet's footprint and drive revenue or growth during renewals Expand Smartsheet brand awareness at the c-suite, operational and team level Facilitate and manage partnerships with Sales Engineers, Solutions Consultants and Customer Success teams to support full sales cycle and close business Create and maintain Joint Engagement Plans for strategic solution deals Maintain accurate and up-to-date records in Salesforce leveraging MEDDICC qualification guidelines to accurately forecast Utilize existing

For over 20 years, Smartsheet has empowered teams to manage work seamlessly and scale solutions smarter. Now, in our most ambitious chapter yet, we are uniting human teams with AI agents. By orchestrating the work agents do best, automating manual tasks and uncovering insights at scale, we create the space for people to focus on what truly matters: judgment, creativity, and big thinking. That is magic at work, and it’s what we show up for every day. Smartsheet is looking for a dynamic Sales Development Representative II to provide sales pipeline generation and revenue-driving activities and help fuel our growth targets for the fiscal year. You will be required to develop a great understanding of our customers, prospect into relevant accounts and utilize outbound efforts to engage and qualify potential customers using various proactive selling efforts. You will be one of the first touch points for prospects and set the tone for the sales cycle following. This role is a great opportunity to sharpen prospecting and discovery skills that align with our Commercial and Enterprise teams. The ideal remote candidate will sit Central to East coast and will report to a Manager of Sales Development in the East. You Will: Partner and work with the Commercial and Enterprise sales teams - including New Business, Expansion, Customer Success, and Professional Services. Work with other Smartsheet teams to develop account knowledge, relationship maps, and use case opportunities through direct account engagement and insight tools Setting qualified prospect meetings with our Sales Executives Strategically prospecting key account targets & contacts Hold thoughtful and engaging conversations over the phone and email Be the subject matter expert on Smartsheet products and services Generate appointments by independently identifying companies and contacts that would be a good fit for our services and making decisions to reach out to them via email, LinkedIn, cold calling, and