saaskicker

Enterprise AE

Celebrated Contributor

[LIVE TODAY] Ask Me Anything - Career Salesperson (SDR -> Ent AE) willing to help.

Launching this live now to hopefully drive questions and engagement, seemed a bit slow yesterday.

I'll circle back periodically and be online from 1-3pm EST today to answer any questions you have.

Re sharing for clarity:

Background about me to help drive questions

-Started as an SDR at a Series A Company

-Have sold for Series A, B, C, D Companies + at a company that IPO'd --> now at a (different) public company

-Moved jobs every 2ish years

-Worked in SF, Denver, NYC & now remote

-Moved from SDR --> now an Enterprise Account Executive at a 500 company

-Have taken courses/trainings throughout my journey

-Sold in the SaaS space for last 10+ years in sales

Happy to answer questions about:

sales (strategy, process, wins/losses)
networking
finding the right company
managing up
getting a promotion
negotiation
best practices in the War Room
interviewing
tech stack
proper discovery
demo best practices
dealing with conflict
stress relievers
anything to help you grow & become a better (sales) person

for those who DM'd me the nasties about me trying to farm commission, I could care less about an amazon gift card, I'm trying to revive this platform to what it used to be & can continue to be --> a place for sales people to swap ideas and have an outlet to grow their own craft, with a side of fun banter.

TLDR: ask me whatever you want, I'll answer, will be live and online this afternoon for rapid responses.

fire away.

👑 Sales Strategy

🚀 Career Goals

26

42 comments

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TennisandSales

Politicker

7

Head Of Sales

hey man if your willing to dedicate 2+ hours on a post you deserve all the commission you get hahaha.

my questions:

what has been the most significant change in the saas space you have seen in the last 10 years.

Ive been in sales for 10 years but only in saas for 6

saaskicker

Celebrated Contributor

4

Enterprise AE

I would say there have been two big shifts that I've noticed over the years.

1. The amount of noise in the market.

-There are more people, products, and channels to access today. In the beginning, it was phone phone phone phone with a little bit of email. Now there are different channels to use to gather information and prospects. Examples: Email capture to download a case study, webinars on best practices & thought leadership, LinkedIn, and targeted ads.

The result: now more than ever you have to make your outreach about the prospect to stand out from the crowd. Hyper personalization is one way, but another way is being an expert in your prospects industry or business. Understand what their day to day looks like and how you can help them achieve something, not what your product does in terms of bells & whistles + buzzwords. There's also a plethora of tools today to help you get this information depending on your ICP.

2. A term called "vertical SaaS" not creating a tool for everyone, but for a specific use case or target.

-Companies are now going after specific segments and niche's. In the past, you created a SaaS company for the masses. Salesforce, for example, created CRM almost every company from a car wash to a bank needs a CRM, they have branched out a bit making changes to the CRM to focus on the specific industries they serve.

-Owning a niche and providing a specific solution to help an exact persona has grown a ton. An example is the rise of Shopify --> help people create not just a website (sorry WordPress) but to create an eCommerce store.

bonus tidbit: I'm closely watching this no-code / low-code wave as I think that unlocks a whole new beast of products and services to sell to the masses.

TennisandSales

Politicker

1

Head Of Sales

solid answer. The vertical saas companies are awesome IMO. i found my way into a leader in a small vertical and its paid off BIG time for me. that experience is SUPER valuable to the other companies that are in that space.

I always try to push ppl to find those niche markets.

saaskicker

Celebrated Contributor

2

Enterprise AE

Growing your network in vertical SaaS is so important, if you can be a thought leader and respected as a source of truth for the industry you will turn the entire industry into an ATM.

TennisandSales

Politicker

0

Head Of Sales

Yeah i totally believe that. I kinda lucked out in the industry I’m in but i know the years i have in it are really valuable at this point

antiASKHOLE

Tycoon

5

Bravado's Resident Asshole

What tends to be your fears or doubts when transitioning or looking into a new position or job?

saaskicker

Celebrated Contributor

7

Enterprise AE

My biggest fear and doubts are not being able to sell the product, therefore making less money, in the end having to start over in a few months looking for a new job.

Here's what I look for on the surface when vetting a new job:
-Where did the sales/exec leadership come from? Have they been successful, did they get acquired or IPO vs. did the company tank and they spun up a new shiny object. I really like to see sales leaders with experience either at competitors or big sales shops - the ones from big sales companies know how much support and enablement is needed to succeed. If they come from start ups that's not a negative, but it shows me they are scrappy want to get shit done & used to operating lean.

-Product market fit: I will actually do a little prospecting mostly in my network to ask "hey what do you think about this solution or product" - most recently I was looking into a tool that was targeted towards smaller VCs to help them operate and distribute capital, luckily I have some connections in that space and asked them if they had heard about it / would the see value in it if they hadn't. In this example, both the people I talked to were already users of said product (good sign).

-Perks/Benefits: this seems silly but most people overlook this and it's a huge part of your "total compensation". Am I going to make the same amount but not get to expense the gym? Do I get free lunch but they don't pay for 100% of my health care? Shit adds up, this is not a make or break for me, but personally, it's important.

antiASKHOLE

Tycoon

2

Bravado's Resident Asshole

Very helpful information, thank you so much for this. I help so many other people look for jobs and placements just as a side courtesy within my network and this helps me refine my process for them as well as for myself.

saaskicker

Celebrated Contributor

1

Enterprise AE

also helps to know what that person wants in their career / where they are at. if i talk to someone who has bounced around a few start ups i'll typically point them towards a bigger org to get the foundation and logo on the resume.

if they love start ups, always check out the investors to see what that looks like - similar to background of the execs.

your network is your net worth in this game, glad to hear you're spreading the wealth.

antiASKHOLE

Tycoon

2

Bravado's Resident Asshole

Thanks man. All very good pointers. much appreciation

Sunbunny31

Politicker

4

Sr Sales Executive 🐰

I'm curious as to why you have changed jobs every 2 or so years. Maybe there are many reasons, but I'd be interested to hear.

saaskicker

Celebrated Contributor

2

Enterprise AE

One job change was due to acquisition, start up I was at got aquired by a company that was about to IPO, entire sales team was let go.

One job change was when I moved from the west coast to the east coast, better opportunity + new company offered to pay for the move, win-win.

One job change was for a title and pay bump. The company I was at was spinning wheels, we couldn't crack the hyper-growth code and I was mopping up SMB deals and hitting a ceiling in both growth and earnings.

Most recently I changed jobs again for a pay bump but also I'm at a phase in my life where health insurance and paternity leave is very important, company I was at was so-so. New company is great logo, opportunity, more money + the value they put on spending time with new kids is priceless.

Two things I've learned.
1. You can love a company but they will never love you back.
2. Best way to get paid more is to switch jobs.

Interesting read for you: https://www.forbes.com/sites/cameronkeng/2014/06/22/employees-that-stay-in-companies-longer-than-2-years-get-paid-50-less/?sh=5527b3cce07f

CuriousFox

WR Officer

3

🦊

Interesting read. Thank you for sharing!

jefe

Arsonist

3

🍁

I was in meetings throughout, but commenting to say thanks and give you some well-deserved commish.

saaskicker

Celebrated Contributor

2

Enterprise AE

for those asking why i don't want to be in leadership ^^^ head of sales jefe in meetings all day on a friday :P

1nbatopshotfan

Politicker

3

Sales

Hey- great work on this. Very cool of you to commit time to this to help generate buzz.

Question: what’s the correct doneness on a steak?

CuriousFox

WR Officer

2

🦊

Rare to med rare.

1nbatopshotfan

Politicker

1

Sales

Med rare? Ehh on occasion I suppose. :-)

CuriousFox

WR Officer

2

🦊

You don't respect the steak. I'm sad. 🦊

1nbatopshotfan

Politicker

1

Sales

I’m always rare. But I get it some steak can go to medium rare.

CuriousFox

WR Officer

2

🦊

Ok you answered this correctly. I have a feeling we'd be the very best of friends. 💯🔥

1nbatopshotfan

Politicker

1

Sales

You already know we are

CuriousFox

WR Officer

2

🦊

TRUTH 🔥🍸

saaskicker

Celebrated Contributor

2

Enterprise AE

130-135 degrees.

butwhy

Politicker

2

Solutions Engineer

Thanks for doing this! We should all take go arounds of AMAs.

How do you address the 2 year job tenure in interviews?

What's your number one priority during procurement (other than "sign sign sign"?

Do you ever miss Startup-land?

saaskicker

Celebrated Contributor

3

Enterprise AE

Addressing tenure: one thing I'm ALWAYS doing no matter if i love my job or not, is interviewing. it is exponentially easier to get a new job when you have a job, that being said these companies have reached out to me based on my "amazing profile" and I can say i was impressed by the company and excited to join.

on the flip side, you always have to have a narrative of why you left. for me that includes.
-hit a ceiling closing SMB deals and had an opportunity to move up to a mid market role, took it, was successful, here we are.

-wanted to expand my knowledge in a certain industry so switch to a different company, did well, learned quick.

-company was acquired and sales team was eliminated

at the end of the day, if you have references and your numbers are good on attainment, people want a top performer in the seat and don't care if you bounce around. last point - it has only come up in an interview process with me one time and the hiring manager asked - and i interview A LOT.

Procurement: you want to get ahead of this before you worry about sign sign sign thoughts. The best advice and practice I can give for this is always use a type of Mutual Close Plan / Mutual Action Plan with your buyer/champion.

Sept 9 - demo
Sept 12 - present pricing
Sept 14 - negotiate terms
Sept 15 - agree to terms
okay mr/mrs prospect how long does procurement take? 1 month?
Sept 16 - submit to procurement
Oct 16 - contract signed
Oct 17 - go live with product X

hold them accountable, have them coach you through their buying process as you have just coached them through the sales process. the more you can have ball control the more time your going to have to not stress about following up or your manager hounding you for updates. my example is trivially but mold it to your own process. i use google sheets and share it was the prospect as a working doc, can tag them and ask for updates when things are behind to make sure you stay on track. -- i could write a whole post on this process, if you can nail this, you will shine + prospects will think you're way smarter than you are.

Do I miss start up land? -- yes absolutely, waiting for the right time to jump back in and take that risk. but nothing is more fun in sales than moving fast and breaking things. my ideal start up is a mid to late series b with 4-5 reps crushing it and just need to come in and sell. i keep an eye on 3-4 year old Y Combinator companies on a weekly/monthly basis to see how they are doing, fun way to keep a pulse on the market and where VC dollars are flowing.

theSADNESSisreal

Executive

2

SAD

This is what it's all about!

Any advice for finding the right company fit? Starting to look at new role, struggling to pin down where to start for series and size since my experience is limited. How do get a read on the culture and what day-to-day is really like in the role if you don't have existing connections within that company.

Cheers!

saaskicker

Celebrated Contributor

2

Enterprise AE

Great question - let me spin this back to you to provide a personal answer.

1. What did you study?
2. If you didn't like what you studied, what gets you excited on a daily basis (doesn't need to be saas/tech related)?
3. How do attempt to get a read on culture today?

theSADNESSisreal

Executive

1

SAD

I see what you did there, well played.

1 - Finance
2 - I like finance just not to pursue most traditional finance careers. More so a side hustle skill set at this point for financial freedom and pursuing real estate investments. Other than that I like golf, travel and fast cars.
3 - Largely been using my network to gain insight. Starting to find some other companies of interest that I don't have direct connections.

saaskicker

Celebrated Contributor

2

Enterprise AE

Awesome - there's so many great FinTech companies out there both established and new. The more you can get ingrained in that the more it'll be fulfilling vs feeling like work.

If you can find a company that sells a financial SaaS product or into a Finance department lastly a bank, you can leverage your domain knowledge to speak the language. i.e. Pipe, Ramp, Brex on the big end of spend management to fin departments. Love Plaid and think what they're doing to democratize finance / fintech is very cool as well. Just some examples of how I would think about it.

so much of enjoying sales is enjoying/respecting who your buyer persona is, many times this gets over looked. think marketing is dumb and a waste of time, hate everyone in that department? probably don't wanna sell an email or ad platform where you prospect marketers all day.

on culture, read the company blog, see if they have a LinkedIn presence or even a youtube channel of "what it's like working for X" - you can understand what voice they put out in the blog, is it stat heavy, old and crunchy? or do they have a quick wit, use emoji's and seem fun - etc etc. companies that invest in videos on culture usually care a lot about it (it may be surface level, everyone is different) but at the end of the day a company with a stiff or terrible culture most of the time won't have a video of how amazing it is to work there.

hope this helps. disclaimer, the companies called out in this answer i have no idea if they are hiring/great sales cultures/etc but those should lead you on the right track to find some other similar companies. just name dropped them to get the juices flowing (and on the surface i've followed them and look cool).

theSADNESSisreal

Executive

2

SAD

Much appreciated @saaskicker! Keep bringing your gift to Bravado!

Not sure how you pulled that off with that set of info. This calls out what I'm struggling with and a great path for moving forward.

saaskicker

Celebrated Contributor

2

Enterprise AE

also seeing an uptick in new and improved commission software, like CaptivateIQ, sell to finance and sales department, some math in there but also helping savages understand how much they get paid.

if real estate side hustle is interesting i'd look into some property management saas as well, gives you a glimpse under the hood.

ThatNewAE

Big Shot

2

Account Executive - Mid enterprise

Q. When you are on a call with a prospect. They like the product, and you know they will definitely sign the contract in the next month. I know you're Ent AE, but if you were to think in a SMB AE's shoes - would you drive the urgency right away knowing that startups change their strategies every week. It's fast and it's risky. Or would you go by your hunch and let them have that time, come back next month?

saaskicker

Celebrated Contributor

4

Enterprise AE

Ask them what could change between now and next month. Why wait?

Another approach is if you are selling a product that provides value or revenue, calculate the cost of doing nothing. If you predict you can increase sales by 100%, it is going to cost them money to wait one month to sign this.

If you have leverage, you can present pricing in a way that incentivizes them to sign today vs next month.
today it's $1,000 and you can do two payments
next month it's $1,000 must be paid up front or it's $1,250 etc etc

if they hold their ground and won't sign you need to have 1-2 calls booked with the DM and champion each week before they sign. stay top of mind, talk about launch strategies, share customer stories, set up reference calls. the more time you have on their calendar, the more they think about you and the LESS time they have to change their mind or look at a competitor.

Kosta_Konfucius

Politicker

2

Sales Rep

Have you ever thought about moving to leadership? If you are doing this it seems like you like coaching .

saaskicker

Celebrated Contributor

4

Enterprise AE

I've had a few opportunities and have considered it. I enjoy coaching and helping others, but have realized that I really enjoy the freedom of being an individual contributor more.

If I want to goof off and answer questions all day on a Friday, I can. If I want to go to Europe for a week and leave my computer behind, I can. If I want to take a two hour lunch and watch the little league world series with friends over a few beers, I can.

Big trade-off, as I prepped and thought about management I just couldn't get over the hump of every single day my calendar being controlled by upper management + my reps calls + 1:1's + building dashboards and forecasting + navigating internally, and politicking.

Kosta_Konfucius

Politicker

1

Sales Rep

Totally makes sense!

Outside of money, what the main motivator being an IC for 110+ years? I know this is an interview questions, but I always feel like I have to say management when asked that

saaskicker

Celebrated Contributor

2

Enterprise AE

I like solving business challenges and introducing them to products.

I enjoy the hunt and rush of prospecting a new account or person & seeing that docusign come through.

I am self aware when it comes to my strengths, and I feel I can provide the most value to company by being an IC.

Power of focus for me, if I can focus on closing business I'll do it very well.

not sure if this is what you're asking for in the follow up q. but this is how i'd answer in an interview. also, being an IC for a long time can also be a managers dream, staying in your lane and putting numbers up while they dont have to micromanage your career / have you taking in multiple projects outside of just hitting your number.

SaaS_Man

Executive

1

BDR - MANNY

MANAGING UP: How do I “convince” the VP of Sales to sign off on SQLs so my BDRs can get paid. She’s a stickler for detail and will challenge them. But they meet the criteria. Already yelled at her twice so I don’t want to get fired.

saaskicker

Celebrated Contributor

1

Enterprise AE

are you the BDR manager?

SaasSlingin

Politicker

0

Sr AE

Say you’re hiring a more jr AE. What are your thoughts on a short stint at a company & taking a break/gap between gigs?

saaskicker

Celebrated Contributor

1

Enterprise AE

It's probably a red flag for a Jr AE in my opinion. Gives off no grit, not able to perform vibes. Need to have a really compelling story.

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