Full-Time

Director - Enterprise Sales

Posted on 11/24/2025

Actively AI

Actively AI

51-200 employees

AI-driven outbound automation for GTM teams

Compensation Overview

$300k - $400k/yr

+ Commission + Equity

San Francisco, CA, USA

In Person

Category
Sales & Account Management (1)
Requirements
  • Two or more years of experience leading Enterprise Account Executive teams in a high-growth startup or scaling environment, with at least four years of management experience.
  • Eight or more years of overall sales experience, including four years of selling into the Enterprise segment.
  • Proven success hiring, coaching, and developing enterprise sales talent.
  • Expertise in enterprise sales methodologies such as MEDDIC, Challenger, and SPIN, and in pipeline management.
  • Strong ability to execute in a fast-paced startup environment with limited resources.
  • Track record of exceeding revenue targets and driving high-performing teams.
  • Excellent strategic thinking, problem-solving, and leadership skills.
Responsibilities
  • Recruit, hire, and develop a high-performing team of Enterprise Account Executives.
  • Coach and mentor Account Executives to improve sales performance, pipeline generation, pipeline management, and deal execution.
  • Own and optimize the enterprise sales process, implementing proven sales methodologies such as MEDDIC, Challenger, and SPIN.
  • Drive a strong pipeline generation culture by establishing an outbound organization that is best in class using Actively AI and other forward-looking technologies.
  • Drive revenue growth by developing and executing strategies to acquire top Enterprise prospects.
  • Collaborate cross-functionally with marketing, product, and customer success to ensure alignment and drive pipeline velocity.
  • Analyze key sales metrics, forecast accurately, and continuously refine the sales playbook based on performance data.
  • Lead by example, participating in high-value enterprise deals and strategic negotiations.

Actively AI builds AI-driven outbound automation tools for GTM teams. Its platform uses AI agents to find the right prospects, decide the best timing, and craft effective outreach, helping sales teams improve pipeline quality and volume. The product operates as a subscription service with tiered plans based on users or service level, charging ongoing fees for access to its AI-driven platform. It differentiates itself by targeting sales and marketing teams with autonomous AI agents that optimize outbound activities, leading to higher sales qualified opportunities and more meetings with fewer resources. The company aims to help go-to-market teams scale their outreach, increase pipeline value, and book more meetings by applying AI to each step of the outbound process.

Company Size

51-200

Company Stage

Series B

Total Funding

$67.5M

Headquarters

New York City, New York

Founded

2016

Simplify Jobs

Simplify's Take

What believers are saying

  • Ramp generated tens of millions in closed-won revenue; Verkada doubled sales productivity using platform.
  • Series B funding of $45M from TCV and First Harmonic validates market demand for autonomous sales agents.
  • Shift from systems of record to systems of action positions Actively as Salesforce alternative.

What critics are saying

  • Salesforce Agentforce 2.0 integrates native autonomous agents, eliminating Actively's bolt-on value proposition.
  • OpenAI integrates advanced sales agent features into ChatGPT Enterprise, capturing GTM teams directly.
  • Anthropic Claude Enterprise Agents offer superior reasoning at lower cost, commoditizing custom agent development.

What makes Actively AI unique

  • Custom reasoning models combining in-house tech with OpenAI and Anthropic deliver 2x conversion rates.
  • Autonomous AI agents execute prospecting, outreach, and workflow management without continuous human intervention.
  • Direct integration with Salesforce, email, and Slack enables seamless deployment into existing GTM stacks.

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Benefits

Health Insurance

Unlimited Paid Time Off

Company Equity

Commuter Benefits

Growth & Insights and Company News

Headcount

6 month growth

-10%

1 year growth

-3%

2 year growth

1%
RSS News Hub
Apr 18th, 2025
Actively AI raises $22.5M for sales reps

Actively AI has secured $22.5 million to enhance its AI-powered sales representatives. Co-founder Anshul Gupta explained that traditional AI sales reps have been unsuccessful due to their focus on sheer volume of contacts. Actively AI aims to differentiate itself by developing custom reasoning capabilities for its sales reps.

PYMNTS
Apr 2nd, 2025
Actively AI Secures $22M for AI Sales

Actively AI has raised $22 million to enhance AI-powered sales reps by focusing on reasoning models rather than volume. Co-founders Anshul Gupta and Mihir Garimella, both Stanford AI alumni, aim to mimic human decision-making to identify high-value prospects. Their "GTM Superintelligence" combines in-house and popular models from OpenAI and Anthropic, differing from generative AI by emphasizing logical reasoning and problem-solving.

TechCrunch
Apr 2nd, 2025
Actively AI raises $22.5M to offer sales ‘superintelligence,’ says AI SDRs failed | TechCrunch

Actively AI argues that most AI sales reps have "failed." It just raised $22.5 million.

Conversion Capital
Mar 28th, 2024
Portfolio Companies Archive

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