Sales Development Executive – Cold Calling & Outbound Sales

We’re looking for an experienced B2B Sales & Cold Calling Specialist who can confidently initiate conversations with business decision-makers, qualify opportunities, build interest, handle objections, and convert outbound outreach into meaningful sales opportunities for Designday.

Designday is a B2B design-technology company working with businesses across digital product design, UX/UI, technology, AI, fintech, SaaS, branding, and digital transformation.

This role is for someone who is genuinely comfortable with cold calling and has experience selling to businesses rather than consumers.

We are particularly interested in candidates who have previously worked with or sold to startups, MSMEs, mid-market companies, and enterprises, as each segment requires a different sales approach, buying conversation, and decision-making process.

Not someone who only sends emails or LinkedIn messages, but someone who can pick up the phone, speak confidently with founders, CXOs, product leaders, marketing leaders, technology teams, and other senior decision-makers, understand their business challenges, and create enough interest to move the conversation forward. You’ll help us expand its business across India, the United States, UAE, United Kingdom, Singapore, Philippines, and other international markets.

Our potential clients include startups, MSMEs, fintech companies, banks, SaaS businesses, technology companies, digital businesses, large enterprises, and organizations undergoing digital transformation.

You will work closely with the founders and business team to identify target companies, understand DesignDay’s capabilities, develop effective outbound approaches, and consistently build a qualified B2B sales pipeline.

Role Description

The ideal candidate understands that successful B2B cold calling is not about reading a script.

It is about quickly understanding who you are speaking with, earning their attention, asking intelligent questions, identifying potential business problems, positioning DesignDay appropriately, and creating a reason for the prospect to continue the conversation.

You should understand that selling to a startup founder is very different from selling to an MSME owner, product leader, or enterprise CXO.

You should be comfortable adapting your conversation based on:

• Company size
• Business maturity
• Industry
• Decision-making structure
• Budget sensitivity
• Procurement complexity
• Urgency
• Strategic importance of the project

You should be comfortable taking a prospect through:

Research → Outreach → Cold Call → Discovery → Qualification → Follow-up → Meeting → Opportunity → Closure

Depending on the opportunity, you may either independently progress the sales conversation or work alongside Designday’s founders and senior team during discovery, proposal, negotiation, and closure.

You should be comfortable selling B2B technology, design, digital transformation, or professional services, where the buying decision may involve multiple stakeholders and require consultative conversations rather than transactional selling.

Preferred Background

Candidates with previous experience selling any of the following will have an advantage B2B technology services, UX/UI design services, Product design, Digital transformation services, Software development, IT services, SaaS products, Technology consulting, Branding and digital services, Fintech solutions, Enterprise technology solutions, Marketing or professional services, B2B consulting services

Strong preference will be given to candidates who have previously qualified delas or worked with:

• Startups
• MSMEs
• Mid-market companies
• Large enterprises
• Fintech companies
• SaaS companies
• Banks and financial institutions
• Technology companies
• Digital-first businesses

Candidates should ideally understand how sales conversations change across different client segments.

Experience speaking with founders, CEOs, CXOs, product heads, CTOs, CMOs, digital transformation leaders, innovation teams, procurement stakeholders, and business owners will be highly preferred.

Experience selling to clients in the US, UAE, UK, India, Singapore, or other international markets will be a strong advantage.

Qualifications

• 2–5 years of experience in B2B cold calling, outbound sales, business development, inside sales, SDR, lead generation, or related roles.
• Demonstrable experience selling B2B services, technology solutions, design services, SaaS, consulting, or professional services.
• Previous experience working with startups, MSMEs, mid-market businesses, or enterprises is highly preferred.
• Demonstrable experience speaking with business decision-makers through outbound calling.
• Previous experience generating meetings or sales opportunities through cold outreach.
• Strong verbal communication and active listening skills.
• Excellent spoken English.
• Strong objection-handling capabilities.
• Ability to communicate confidently with senior business stakeholders.
• Ability to understand client requirements and identify underlying business problems.
• Understanding of different B2B buying cycles across startups, MSMEs, and enterprises.
• Experience managing multiple follow-ups and longer B2B sales cycles.
• Comfortable working with targets, KPIs, and performance metrics.
• Comfortable using CRM systems, prospecting tools, LinkedIn, email, and sales engagement platforms.
• Strong ownership mentality and ability to work independently.

Education & Preferred Academic Background

• Bachelor’s degree in Business Administration, Marketing, Sales, Commerce, Management, Communications, or a related field is preferred.
• An MBA or postgraduate qualification in Marketing, Sales, International Business, or Business Management will be an advantage, particularly for candidates handling enterprise and international B2B accounts.
• However, strong practical B2B sales experience, cold-calling capability, and a proven track record of generating and closing opportunities will be valued more highly than academic qualifications alone.
• Candidates with relevant experience in technology services, SaaS, IT services, design, consulting, digital transformation, or professional services sales will be strongly preferred.

What You Get Working With Us

This role gives you more than just a sales target. You’ll gain exposure to how different businesses buy, how founders and CXOs evaluate strategic partners, how complex B2B deals move from first conversation to closure, and how strong positioning can influence high-value opportunities.

You’ll work closely with the founders and internal teams, giving you direct visibility into client conversations, proposals, commercial discussions, and decision-making. As you perform, you’ll have the opportunity to take ownership of larger accounts, international markets, strategic opportunities, and eventually broader sales responsibilities.

With a competitive fixed package and performance-linked incentives on successful closures, your growth and earning potential will be directly connected to the business you help create.

Why Join Designday?

Designday is a B2B technology and design company helping businesses build better digital products, experiences, and platforms.

We work with companies across UX/UI, product design, fintech, SaaS, AI, technology, branding, and digital transformation, which means you’ll be selling solutions that solve real business problems rather than pushing a generic product.

If you enjoy opening new conversations, speaking with founders and senior decision-makers, understanding businesses, building relationships, navigating objections, and turning opportunities into revenue, this role will give you the space to build those skills at a much deeper level.

You won’t just be measured by how many calls you make.

You’ll be measured by the quality of opportunities you create, the relationships you build, and the business you help us to close deals.