Sales Leadership Hiring for Start-ups

About the speaker

Siddharth is a seasoned Business Leader and an expert at Talent Strategy. In his current role, he is the Director & Head – Talent Strategy at Lightspeed India Partners Advisors. He is responsible for working with founders to build a point-of-view around talent. He helps Lightspeed portfolio companies around Organisation Structuring, Assessment, Coaching, Hiring Partner network and CXO talent.

In this samvaad, I will speak to Siddharth about sales leadership hiring at start-ups, their point of view on hiring sales leadership talent and what they look for.

Topics covered

• Basics of building your sales team
• Frameworks for identifying sales talent
• Availability of talent for tech companies in India
• Where should one look for sales talent: agencies/references
• Interviewing for sales roles
• Onboarding sales leadership talent
• Compensation for sales leadership
• What sectors should ne hire from?
• Top takeaways on sales hiring for founders

Call notes

Saurabh: Building Sales teams and Leadership – How do you build that up? Not just senior leadership, but the middle layer as well?

When leadership in your portfolio companies are beginning out, What do they tell you? Are they able to define their requirements clearly? What kind of conversations are these?

Siddharth: It’s a relevant space that you’ve picked out. First-time founders generally don’t come from a GTM background, they are typically from a product/technology background.

GTM seems like a mystical ball. Nobody is really clear upfront about what’s to be done. We try to sit and prioritize what’s relevant and important for them

What we try to do with the founder up front 

• Drill down and identify the stage the firm is at
• Based on this, define what needs to be done in this and the next 2 stages

Hiring and defining the role of a sales leader differs at a 0-1 / 1-10 / 10-100 stage.

Saurabh: Do you see them come to you after having burnt their fingers by hiring themselves?

Siddharth: It does happen, but we try not to let it get there for our portfolio companies.

What we try to do is assist in defining what a good sales leader looks like – identifying 

1. What are you hiring for? 
2. How are you evaluating what you are hiring for? 
3. How do you manage the person once they are on board?

Saurabh: Do you have some frameworks to identify this talent?

Siddharth: Typically the brief from the founder is a single line. Things like – “I have to get to x revenue stage” | “I have to get to a certain number of users/merchants on board” or something to that effect

At the 0-1 stage – The Evangelist. Founders are best suited for this – founders are the most passionate and will always sell at any opportunity. We recommend that they get their first set of clients on board themselves.

At the 1-10 stage – The Hustler – Working with 5-10 sales reps – here we’re looking for someone to come in and set up a repeatable sales playbook – a professional. 

It’s predominantly going to be someone who is a recent quota carrier with a lot of hustle and is looking to win at all costs. 

Also best to look for someone who has recently created a sales playbook.

This person should also be able to get insights from clients and move quickly.

At the 10-100 stage – The Professional – here the sales playbook should be repeatable and process driven, Coaching, culture, recruitment skills are key at this stage.

Look for experienced pros who have done this before.

Saurabh: In your experience, I assume these are people who may come from outside tech. Are you able to get enough talent in India from tech companies?

Siddharth: If you had asked me this 5 years ago I would have said no. Over the last couple of years, we can go to companies who have recently been at these stages and find people not necessarily even at higher levels.

However, this pool is still not deep enough and at times we need to go outside. The nuance here is that it does depend on the stage of the company.

Saurabh: When people come in from bigger companies do you see them finding it difficult?

Siddharth: I don’t want to generalize, but personally I see that the hustle is missing. 

People coming in from larger orgs have a lot of resources at their disposal which you don’t have at these startups and you have to get your hands dirty, some people are challenged here.

Saurabh: Taking a step back, the questions I get from founders often – “Where should I look for sales talent?” 

I think this comes from the fact that talent on job portals doesn’t cut it and working with agencies is uncomfortable while doing outbound recruitment.

What would you say to these people?

Siddharth: I don’t think this is only relevant to sales but to every role in your core team. Your first few leaders have to be “Talent Magnets”. They have to be capable of building a following.

Try and find out how many people follow these people across companies, teams etc.

Saurabh: How do you find that out?

Siddharth: Ask them straight up: Questions like: 

“How many people followed you in the last 3-4 organizations?”  

“Tell me who are the best performing people in your team” 

Questions around quota achievement of team members and how many people don’t get to it. 

“Over the last 2 stints, how many people within your teams have gone on to be sales leaders?”

These should give you good indications of – 

1. Are they capable of creating good sales people repeatedly
2. They come with solid references of these people they have already spent time building

References / Reference hires are extremely potent. 

I do tell founders to do 360 references when hiring sales leaders. 10/10 references and glowing recommendations aren’t necessarily great. 

General references aren’t very insightful. 

Know what you are hiring for, know the Gaps and take these to your reference calls!

Saurabh: Do founders need to be working with outbound agencies?

Siddharth: Not as much. I’d say the best way to start is references. Usually it’s never agencies when you are starting off. 

Cold hiring will be a low priority in this case and I would not suggest this up front.

Leverage your network and references.

Saurabh: So building a solid network seems to be critical up front to ensure you get the right talent.

Siddharth: Yes, that’s bang-on.

Saurabh: One concern I have with founders interviewing sales leaders is that they are too used to hiring technology talent and they come with the same mindset to sales interviews. 

What kind of changes do they need to make to interview for sales?

Siddharth: Very relevant. What we’ve done is we divide what to evaluate for a sales leader. We ask them to start with 

• common things like- culture fit, work ethic – founders can do this part themselves as it doesn’t change for roles
• For sales / technical part of the interview – we recommend this be done with an experienced sales leader. We have founders have initial conversation and bring in external “technical experts” / experienced sales leaders to have these conversations with inputs with the founders with founders shadowing them and observing to learn the nuances of these conversations

Saurabh: On onboarding sales leadership talent: 

What challenges have you seen? 

Siddharth: Where it doesn’t work out is poor expectation setting. Expectations set in interviews vs. what they are expected to do once they join don’t match.

Some leaders tend to do the same things that they hire these leaders to do and responsibilities overlap. These people are brought on board as experts.

I typically tell founders to pick the right people and enable them with the right resources to make decisions themselves.

Saurabh: It’s speculated that if you’re coming from an established industry / organization and joining a startup, you will have to sacrifice compensation – how far is this true?

Siddharth: It’s not true, however, I’ll caveat that with the fact that we tell founders to have discussions with a long view (5 years) and it depends on the stage of the company you are joining, potential growth pace and opportunity

If you are coming into an early stage firm you may sacrifice on cash early on but there will be significant long term upside in the form of ESOPs, growth pace etc. 

We also tell these leaders to use this 6 month – 1 year ramp up time to figure out whether this is working for them or not.

Audience question: If we’re trying to hire from the FMCG sector, what are your views on bringing these people in at the product market fit stage?

Siddharth: We’ve hired a lot from these sectors and we suggest founders to bring these people in at the growth stage and perhaps not at a very early stage if they have no prior startup experience.

What you’re really getting from these folks is the ability to scale things really fast. They are great “scalers”.

If the same person has startup experience already, creating sales playbooks, this is a fantastic hire.

Saurabh: In closing, what would you suggest founders keep in mind, top 3-4 things?

Siddharth:

     Few things: 

1. Go Benchmark what / who you consider to be a good sales leader – talk to these people about what you should be looking for. Ask them if they’d be keen to come in as experts to help you evaluate talent

2. When you bring sales leaders on board, remind yourself that you have trusted these people and they have gone through your evaluation cycle – give them the space to make decisions

3. Do deep reference checks. Be on these calls yourself. Do not outsource this.

      4. If things don’t work out in a reasonable time, take quick calls