Enterprise Account Executive, Siro

$250-350k

OTE

+ Offers Equity + Offers Commission

Expert level

New York

More information about location

Office located in Flatiron, NY

AI coach for field sales reps

Open for applications

AI coach for field sales reps

21-100 employees

B2BArtificial IntelligenceTrainingLearningSales

Open for applications

$250-350k

OTE

+ Offers Equity + Offers Commission

Expert level

New York

More information about location

Office located in Flatiron, NY

21-100 employees

B2BArtificial IntelligenceTrainingLearningSales

Company mission

Siro's mission is to create a world where anyone can find social mobility and financial freedom through a career in sales.

Job

Company

Role

Who you are

~10+ years of enterprise level B2B SaaS sales experience, hunting new logos and managing complex sales processes
Proven track record of exceeding large quotas
An existing network and the ability to create relationships with key stakeholders within target verticals
Deep experience selling to C‑suite / executives in large organizations
Strong ability to generate leads, build pipeline, and close enterprise deals with minimal assistance
Excellent communication & presentation skills; ability to tell compelling stories; confidence in executive level conversations
Self‑motivated, highly organized, resilient; you’re comfortable working independently in ambiguity and forging paths

What the job involves

We are seeking an outstanding Enterprise Sales Director who lives to hunt
This person will play a critical role in expanding our footprint among enterprise level clients: identifying strategic opportunities, penetrating accounts and existing partnerships, and establishing long‑term relationships
You’ll be a key member of our sales org, working closely with Marketing, Customer Success, Product, and Leadership
Develop and execute a strategy to source, pursue, and close new enterprise customers in target verticals (e.g., Fortune 500, industry leaders)
Hunt new business: cold outreach (calls, emails, social), leveraging networks, referrals, events, etc
Own the full sales cycle from initial outreach through contract negotiation and signing
Build, maintain, and grow a pipeline of high‑value opportunities; forecast with accuracy and drive predictable revenue
Partner cross‑functionally: collaborate with Marketing to align on lead gen and content; with Product to feed customer insights; with Customer Success to ensure smooth onboarding and account management
Serve as a thought partner and subject matter expert: present to C‑level executives, position the product in strategic conversations, act as the face of our enterprise go‑to‑market
Provide feedback to leadership on market trends, competitive intelligence, pricing, packaging

Our take

The activities of sales representatives are essential for maximizing the profits of a business, but it’s difficult to optimize this when there is no efficient way of tracking conversations. It is almost impossible to know exactly how long a sales rep pitches a product or exactly what they said, and this makes it difficult for businesses to improve their sales.

Siro provides a digital mobile and desktop app that facilitates the tracking and analysis of the conversations of sales reps and clients. The app records and transcribes sales conversations, providing a quantifiable footprint of every sales conversation which can then be analyzed by sales managers for improvements.

Whilst the recording and transcription software behind Siro is nothing new, the integrated approach to tracking sales conversations is one that has been untapped until now. The company claims that when used properly, its sales coaching system can reduce sales conversation time tenfold - giving Siro the potential to take sales coaching to a whole new level.

Freddie

Company Specialist at Welcome to the Jungle

Insights

Top investors

Glassdoor (4.7)

Company

Funding (last 2 of 4 rounds)

May 2025

$50m

SERIES B

Oct 2023

$14m

SERIES A

Total funding: $69.1m

Company HQ

Flatiron District, New York, NY

Leadership

Jake Cronin

(CEO & Founder)

Co-founder of Queue. Was a Woodruff Scholar at Emory where they studied Math, CS, and Chinese Studies. Opened & ran a Cutco branch office.

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